Name: 56453-88-4|(E)-3-(Cyclohex-1-en-1-yl)acrylic acid|97%
Brand: Ambeed
SKU: A1353291
Price: 46.0 USD
Availability: InStock
Rating: 98 (22 reviews)

1
[ 931-49-7 ]
[ 124-38-9 ]
[ 56453-88-4 ]
[ 52467-23-9 ]
[ 139911-59-4 ]

Yield	Reaction Conditions	Operation in experiment
25%	With tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Derien, Sylvie; Clinet, Jean-Claude; Dunach, Elisabet; Perichon, Jacques [Journal of Organometallic Chemistry, 1992, vol. 424, # 2, p. 213 - 224]

2
[ 201230-82-2 ]
[ 78-27-3 ]
[ 56453-88-4 ]

Yield	Reaction Conditions	Operation in experiment
64%	In tetrahydrofuran at 100℃; for 48h;

Reference： [1]Huh, Keun-Tae; Orita, Akihiro; Alper, Howard [Journal of Organic Chemistry, 1993, vol. 58, # 25, p. 6956 - 6957]

3
[ 54526-84-0 ]
[ 56453-88-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydroxide In methanol at 65 - 67℃; for 2h;
84 g	With sodium hydroxide In ethanol for 2.5h; Heating;

Reference： [1]Lai, Gaifa; McAllister, Timothy [Synthetic Communications, 1999, vol. 29, # 3, p. 409 - 413]
[2]Chackalamannil, Samuel; Davies, Robert J.; Wang, Yuguang; Asberom, Theodros; Doller, Dario; Wong, Jesse; Leone, Daria; McPhail, Andrew T. [Journal of Organic Chemistry, 1999, vol. 64, # 6, p. 1932 - 1940]

4
[ 931-49-7 ]
[ 124-38-9 ]
[ 56453-88-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0℃; for 2h;

Reference： [1]Saito, Shinichi; Nakagawa, Satomi; Koizumi, Toru; Hirayama, Kyoko; Yamamoto, Yoshinori [Journal of Organic Chemistry, 1999, vol. 64, # 11, p. 3975 - 3978]

5
[ 56453-88-4 ]
(Z)-(S)-6-Trimethylsilanyl-hex-3-en-5-yn-2-ol [ No CAS ]
[ 222972-45-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;	2.4 Step 4 To a solution of the deprotected enyne from above in anhydrous CH2Cl2 (30 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.412 g, 23.01 mmol), dimethylaminopyridine (DMAP) (2.836 g, 23.2 mmol), TEMPO (1 mg), and dienoic acid 3 (2.414 g, 15.9 mmol). The reaction mixture was stirred at room temperature under argon for 18 h. The solvents were removed and the mixture was diluted with EtOAc (300 ml). The organic phase was washed with water (150 ml), 0.5 N HCl solution (2 x 100 ml), and brine (100 ml) and dried over anhydrous MgSO4. Evaporation under reduced pressure yielded the ester 12 as a brown oil (2.601 g, 83%). An analytical sample was prepared by further chromatography on silica gel (5% EtOAc in hexane). [α]D25 +190.7 (c 1.04, CHCl3); IR (CH2Cl2) 2151, 1715 cm-1; 1H NMR (400 MHz, CDCl3) δ 0.20 (s, 9H, C(CH3)3), 1.40 (d, J=6.4 Hz, 3H, CH3), 1.58-1.66 (m, 2 H, CH2), 1.66-1.73 (m, 2 H, CH2), 2.10-2.18 (m, 2 H, CH2), 2.23-2.30 (m, 2H, CH2), 5.57 (dd, J=11.0, 1.1 Hz, 1 H, C=CH), 5.76 (d, J=15.6 Hz, 1 H, CH=C), 5.86 (dq, J=6.44, 7.56 Hz, 1 H, CH=C), 5.97 (dd, J=7.8, 11.0 Hz, 1 H, CH=C), 6.22 (t (broad), J=4.0 Hz, CH=C), 7.31 (s, 1 H, CH=C); 13C NMR (100 MHz, CDCl3) δ -0.203, 19.81, 21.98, 22.01, 24.07, 26.40, 69.02, 100.20, 101.51, 110.35, 114.55, 134.85, 138.77, 143.55, 148.21, 166.65; HRMS (FAB): Calcd for C18H27O2Si (M+) m/e 302.1702, found m/e 302.1695.
2.601 g	With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 18h; Ambient temperature;

Reference： [1]Current Patent Assignee: MERCK & CO INC - EP1036072, 2004, B1 Location in patent: Page 60
[2]Chackalamannil, Samuel; Davies, Robert J.; Wang, Yuguang; Asberom, Theodros; Doller, Dario; Wong, Jesse; Leone, Daria; McPhail, Andrew T. [Journal of Organic Chemistry, 1999, vol. 64, # 6, p. 1932 - 1940]

6
[ 471-25-0 ]
[ 56453-88-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	In diethyl ether at -10℃; for 1h;

Reference： [1]Alexakis, A.; Normant, J. F. [Tetrahedron Letters, 1982, vol. 23, p. 5151 - 5154]

7
[ 882158-71-6 ]
[ 56453-88-4 ]
[ 905572-61-4 ]

Yield	Reaction Conditions	Operation in experiment
63%	With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane
	With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;

Reference： [1]Clasby, Martin C.; Chackalamannil, Samuel; Czarniecki, Michael; Doller, Dario; Eagen, Keith; Greenlee, William J.; Lin, Yan; Tsai, Hsingan; Xia, Yan; Ahn, Ho-Sam; Agans-Fantuzzi, Jacqueline; Boykow, George; Chintala, Madhu; Foster, Carolyn; Bryant, Matthew; Lau, Janice [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 6, p. 1544 - 1548]
[2]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

8
[ 226915-53-3 ]
[ 56453-88-4 ]
[ 226915-55-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;
63%	With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane
63%	Stage #1: (E)-3-(1-cyclohexen-1-yl)-2-propenoic acid With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 0.166667h; Stage #2: (2R)-4-hydroxypentyl-2-ynoic acid benzyl ester In dichloromethane for 2h;	1.3 Step 3 trans-3-(1-Cyclohexenyl)acrylic acid (4.13 g, 0.0273 mol) and 4-pyrrolidinopyridine (0.4 g, 10 mol %) in CH2Cl2 (100 ml) were stirred at 0°C. 1,3 Dicyclohexylcarbodiimide (5.63 g, 1 eq) was added and the mixture stirred for 10 min. A solution of the product of Step 2 (5.58 g, 0.0273 mol) in CH2Cl2 (40 ml) was added dropwise. The resulting mixture was stirred for 2 hs, filtered, concentrated and chromatographed (SiO2, 97:3 hexane/EtOAc) to give 5.82 g (63 %) of the desired product.1H NMR (CDCl3) δ 1.61 (d, J = 7.0 Hz, 3H), 1.66 (m, 2H), 1.74 (m, 2H), 2.18 (m, 2H), 2.27 (m, 2H), 5.25 (s, 2H), 5.67 (m, 1H), 5.80 (d, J= 15.0 Hz, 1H), 6.26 (br s, 1H), 7.37 (d, J = 15.0 Hz, 1H), 7.42 (s, 5H).

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]
[2]Clasby, Martin C.; Chackalamannil, Samuel; Czarniecki, Michael; Doller, Dario; Eagen, Keith; Greenlee, William J.; Lin, Yan; Tsai, Hsingan; Xia, Yan; Ahn, Ho-Sam; Agans-Fantuzzi, Jacqueline; Boykow, George; Chintala, Madhu; Foster, Carolyn; Bryant, Matthew; Lau, Janice [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 6, p. 1544 - 1548]
[3]Current Patent Assignee: MERCK & CO INC - EP1036072, 2004, B1 Location in patent: Page 19

9
[ 56453-88-4 ]
[ 344335-60-0 ]
[ 344335-56-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane

Reference： [1]Chackalamannil; Davies; McPhail [Organic letters, 2001, vol. 3, # 10, p. 1427 - 1429]

10
[ 764-01-2 ]
[ 56453-88-4 ]
2-butynyl (2E)-3-cyclohexenylacrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 4h;

Reference： [1]Saito, Akio; Ono, Takamitsu; Hanzawa, Yuji [Journal of Organic Chemistry, 2006, vol. 71, # 17, p. 6437 - 6443]

11
[ 56453-88-4 ]
[ 226915-61-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 63 percent / DCC; 4-pyrrolidinylpyridine / CH₂Cl₂ 2: H₂; TEA / Lindlar catalyst / tetrahydrofuran 3: xylene / 185 °C 4: DBU / tetrahydrofuran 5: 75 percent / H₂ / PtO₂ / methanol 6: (COCl)2; DMF / CH₂Cl₂ 7: Bu₃SnH; Pd(Ph₃P)4 / toluene / 0 - 20 °C
	Multi-step reaction with 5 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h

Reference： [1]Clasby, Martin C.; Chackalamannil, Samuel; Czarniecki, Michael; Doller, Dario; Eagen, Keith; Greenlee, William J.; Lin, Yan; Tsai, Hsingan; Xia, Yan; Ahn, Ho-Sam; Agans-Fantuzzi, Jacqueline; Boykow, George; Chintala, Madhu; Foster, Carolyn; Bryant, Matthew; Lau, Janice [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 6, p. 1544 - 1548]
[2]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

12
[ 56453-88-4 ]
[ 226915-59-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 63 percent / DCC; 4-pyrrolidinylpyridine / CH₂Cl₂ 2: H₂; TEA / Lindlar catalyst / tetrahydrofuran 3: xylene / 185 °C 4: DBU / tetrahydrofuran 5: 75 percent / H₂ / PtO₂ / methanol
	Multi-step reaction with 4 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr

Reference： [1]Clasby, Martin C.; Chackalamannil, Samuel; Czarniecki, Michael; Doller, Dario; Eagen, Keith; Greenlee, William J.; Lin, Yan; Tsai, Hsingan; Xia, Yan; Ahn, Ho-Sam; Agans-Fantuzzi, Jacqueline; Boykow, George; Chintala, Madhu; Foster, Carolyn; Bryant, Matthew; Lau, Janice [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 6, p. 1544 - 1548]
[2]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

13
[ 56453-88-4 ]
[ 866888-52-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 63 percent / DCC; 4-pyrrolidinylpyridine / CH₂Cl₂ 2: H₂; TEA / Lindlar catalyst / tetrahydrofuran
	Multi-step reaction with 2 steps 1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr

Reference： [1]Clasby, Martin C.; Chackalamannil, Samuel; Czarniecki, Michael; Doller, Dario; Eagen, Keith; Greenlee, William J.; Lin, Yan; Tsai, Hsingan; Xia, Yan; Ahn, Ho-Sam; Agans-Fantuzzi, Jacqueline; Boykow, George; Chintala, Madhu; Foster, Carolyn; Bryant, Matthew; Lau, Janice [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 6, p. 1544 - 1548]
[2]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

14
[ 56453-88-4 ]
[ 226915-57-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 63 percent / DCC; 4-pyrrolidinylpyridine / CH₂Cl₂ 2: H₂; TEA / Lindlar catalyst / tetrahydrofuran 3: xylene / 185 °C 4: DBU / tetrahydrofuran
	Multi-step reaction with 3 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C

Reference： [1]Clasby, Martin C.; Chackalamannil, Samuel; Czarniecki, Michael; Doller, Dario; Eagen, Keith; Greenlee, William J.; Lin, Yan; Tsai, Hsingan; Xia, Yan; Ahn, Ho-Sam; Agans-Fantuzzi, Jacqueline; Boykow, George; Chintala, Madhu; Foster, Carolyn; Bryant, Matthew; Lau, Janice [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 6, p. 1544 - 1548]
[2]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

15
[ 56453-88-4 ]
(3S,3aR,4R,4aS,8aR,9aS)-3-Methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 63 percent / DCC; 4-pyrrolidinylpyridine / CH₂Cl₂ 2: H₂; TEA / Lindlar catalyst / tetrahydrofuran 3: xylene / 185 °C 4: DBU / tetrahydrofuran 5: 75 percent / H₂ / PtO₂ / methanol 6: (COCl)2; DMF / CH₂Cl₂ 7: Bu₃SnH; Pd(PPh₃)4 / toluene / 0 - 20 °C
	Multi-step reaction with 5 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h

Reference： [1]Clasby, Martin C.; Chackalamannil, Samuel; Czarniecki, Michael; Doller, Dario; Eagen, Keith; Greenlee, William J.; Lin, Yan; Tsai, Hsingan; Xia, Yan; Ahn, Ho-Sam; Agans-Fantuzzi, Jacqueline; Boykow, George; Chintala, Madhu; Foster, Carolyn; Bryant, Matthew; Lau, Janice [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 6, p. 1544 - 1548]
[2]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

16
[ 56453-88-4 ]
(3R,3aR,4S,4aR,8aS,9aR)-3-Methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 63 percent / DCC; 4-pyrrolidinylpyridine / CH₂Cl₂ 2: H₂; TEA / Lindlar catalyst / tetrahydrofuran 3: xylene / 185 °C 4: DBU / tetrahydrofuran 5: 75 percent / H₂ / PtO₂ / methanol
	Multi-step reaction with 4 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr

Reference： [1]Clasby, Martin C.; Chackalamannil, Samuel; Czarniecki, Michael; Doller, Dario; Eagen, Keith; Greenlee, William J.; Lin, Yan; Tsai, Hsingan; Xia, Yan; Ahn, Ho-Sam; Agans-Fantuzzi, Jacqueline; Boykow, George; Chintala, Madhu; Foster, Carolyn; Bryant, Matthew; Lau, Janice [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 6, p. 1544 - 1548]
[2]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

17
[ 56453-88-4 ]
[ 882158-73-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 63 percent / DCC; 4-pyrrolidinylpyridine / CH₂Cl₂ 2: H₂; TEA / Lindlar catalyst / tetrahydrofuran
	Multi-step reaction with 2 steps 1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr

Reference： [1]Clasby, Martin C.; Chackalamannil, Samuel; Czarniecki, Michael; Doller, Dario; Eagen, Keith; Greenlee, William J.; Lin, Yan; Tsai, Hsingan; Xia, Yan; Ahn, Ho-Sam; Agans-Fantuzzi, Jacqueline; Boykow, George; Chintala, Madhu; Foster, Carolyn; Bryant, Matthew; Lau, Janice [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 6, p. 1544 - 1548]
[2]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

18
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-3-Methyl-4-((E)-2-pyridin-2-yl-vinyl)-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 6.2: tetrahydrofuran; hexane / 20 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

19
[ 56453-88-4 ]
(3aR,4S,4aS,9aR)-3-Methyl-1-oxo-1,3,3a,4,4a,5,6,7,8,9a-decahydro-naphtho[2,3-c]furan-4-carboxylic acid benzyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

20
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-3-Methyl-4-[(E)-2-(5-methyl-pyridin-2-yl)-vinyl]-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 6.2: 74 percent / tetrahydrofuran; hexane / 20 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

21
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-3-Methyl-4-[(E)-2-(6-methyl-pyridin-2-yl)-vinyl]-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 20 °C 6.2: tetrahydrofuran; hexane / 20 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

22
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-3-Methyl-4-[(E)-2-(3-methyl-pyridin-2-yl)-vinyl]-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 6.2: tetrahydrofuran; hexane / 20 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

23
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-3-Methyl-4-[(E)-2-(4-methyl-pyridin-2-yl)-vinyl]-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 6.2: tetrahydrofuran; hexane / 20 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

24
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-[(E)-2-(5-Methoxy-pyridin-2-yl)-vinyl]-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: 58 percent / tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: 99 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

25
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-[2-(5-hydroxypyridin-2-yl)vinyl]-3-methyldecahydronaphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

26
[ 56453-88-4 ]
(3SR,3aRS,4RS,4aSR,8aRS,9aSR)-4-[2-(5-hydroxypyridin-2-yl)vinyl]-3-methyldecahydronaphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: 58 percent / tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: 99 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

27
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-[(E)-2-(6-Ethyl-pyridin-2-yl)-vinyl]-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 6.2: tetrahydrofuran; hexane / 20 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

28
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-[(E)-2-(5-Benzyl-pyridin-2-yl)-vinyl]-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: PdCl₂(dppf)

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

29
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-[(E)-2-(5-Benzyl-pyridin-2-yl)-vinyl]-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: 58 percent / tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: 99 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: 74 percent / Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: PdCl₂(dppf)

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

30
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-{(E)-2-[5-(3-Fluoro-phenyl)-pyridin-2-yl]-vinyl}-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / 16 h / 120 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

31
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-{(E)-2-[5-(3-Chloro-phenyl)-pyridin-2-yl]-vinyl}-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: diboron pinacol ester; KOAc; 1,1'-bis(diphenylphosphino)ferrocine / dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)CH₂Cl₂ / dioxane / 2 h / 80 °C 9.2: 85 percent / K₃PO₄; dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)CH₂Cl₂ / dioxane / 16 h / 80 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

32
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-{(E)-2-[5-(4-Chloro-phenyl)-pyridin-2-yl]-vinyl}-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: 58 percent / tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: 99 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: 74 percent / Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / 16 h / 120 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

33
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-{(E)-2-[5-(2-Chloro-phenyl)-pyridin-2-yl]-vinyl}-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / 16 h / 120 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

34
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-{(E)-2-[5-(4-Fluoro-phenyl)-pyridin-2-yl]-vinyl}-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: 58 percent / tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: 99 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: 74 percent / Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / 16 h / 120 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

35
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-{(E)-2-[5-(2-Fluoro-phenyl)-pyridin-2-yl]-vinyl}-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / 16 h / 120 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

36
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-{(E)-2-[5-(2-Methoxy-phenyl)-pyridin-2-yl]-vinyl}-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / 16 h / 120 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

37
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-[(E)-2-(5-Benzyloxy-pyridin-2-yl)-vinyl]-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: 58 percent / tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: 99 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

38
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-3-Methyl-4-[(E)-2-(5-o-tolyl-pyridin-2-yl)-vinyl]-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / 16 h / 120 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

39
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-3-Methyl-4-[(E)-2-(5-m-tolyl-pyridin-2-yl)-vinyl]-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: diboron pinacol ester; KOAc; 1,1'-bis(diphenylphosphino)ferrocine / dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)CH₂Cl₂ / dioxane / 2 h / 80 °C 9.2: K₃PO₄; dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)CH₂Cl₂ / dioxane / 16 h / 80 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

40
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-{(E)-2-[5-(3-Methoxy-phenyl)-pyridin-2-yl]-vinyl}-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: diboron pinacol ester; KOAc; 1,1'-bis(diphenylphosphino)ferrocine / dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)CH₂Cl₂ / dioxane / 2 h / 80 °C 9.2: K₃PO₄; dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)CH₂Cl₂ / dioxane / 16 h / 80 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

41
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-{(E)-2-[5-(4-Methoxy-phenyl)-pyridin-2-yl]-vinyl}-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: 58 percent / tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: 99 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: 74 percent / Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: 71 percent / aq. K₂CO₃; Pd(PPh₃)4 / toluene; ethanol / 16 h / 120 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

42
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-{(E)-2-[5-(3-Bromo-phenyl)-pyridin-2-yl]-vinyl}-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: diboron pinacol ester; KOAc; 1,1'-bis(diphenylphosphino)ferrocine / dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)CH₂Cl₂ / dioxane / 2 h / 80 °C 9.2: K₃PO₄; dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)CH₂Cl₂ / dioxane / 16 h / 80 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

43
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-4-{(E)-2-[5-(3-Isopropyl-phenyl)-pyridin-2-yl]-vinyl}-3-methyl-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: diboron pinacol ester; KOAc; 1,1'-bis(diphenylphosphino)ferrocine / dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)CH₂Cl₂ / dioxane / 2 h / 80 °C 9.2: K₃PO₄; dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)CH₂Cl₂ / dioxane / 16 h / 80 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

44
[ 56453-88-4 ]
(3R,3aS,4S,4aR,8aS,9aR)-3-Methyl-4-[(E)-2-(5-triisopropylsilanyloxy-pyridin-2-yl)-vinyl]-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

45
[ 56453-88-4 ]
(3S,3aR,4R,4aS,8aR,9aS)-3-Methyl-4-[(E)-2-(5-triisopropylsilanyloxy-pyridin-2-yl)-vinyl]-decahydro-naphtho[2,3-c]furan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: 58 percent / tetrahydrofuran; hexane / 0.17 h / 20 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

46
[ 56453-88-4 ]
3-{6-[(E)-2-((3R,3aS,4S,4aR,8aS,9aR)-3-Methyl-1-oxo-dodecahydro-naphtho[2,3-c]furan-4-yl)-vinyl]-pyridin-3-yl}-benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C 9.1: diboron pinacol ester; KOAc; 1,1'-bis(diphenylphosphino)ferrocine / dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)CH₂Cl₂ / dioxane / 2 h / 80 °C 9.2: K₃PO₄; dichloro[1,1'-bis(diphenylphosphino)ferrocine]Pd(II)CH₂Cl₂ / dioxane / 16 h / 80 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

47
[ 56453-88-4 ]
[ 226914-76-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 63 percent / 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: 66 percent / DBU / xylene / 0.5 h / 20 °C 4.1: 75 percent / H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: 88 percent / Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: Et₃N / CH₂Cl₂ / 0.17 h / 20 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

48
[ 56453-88-4 ]
(3SR,3aRS,4RS,4aSR,8aRS,9aSR)-trifluoromethanesulfonic acid 6-[2-(3-methyl-1-oxododecahydronaphtho[2,3-c]furan-4-yl)vinyl]pyridin-3-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 4-pyrrolidinopyridine; DCC / CH₂Cl₂ / 2 h / 0 °C 2.1: H₂; Et₃N / Lindlar catalyst / tetrahydrofuran / 16 h / 760 Torr 3.1: xylene / 6 h / 210 °C 3.2: DBU / xylene / 0.5 h / 20 °C 4.1: H₂ / PtO₂ / methanol / 16 h / 3102.89 Torr 5.1: SOCl₂ / toluene / 16 h / 80 °C 5.2: Bu₃SnH; Pd(Ph₃P)4 / toluene / 1.5 h 6.1: n-BuLi / tetrahydrofuran; hexane / 0.08 h / 20 °C 6.2: 58 percent / tetrahydrofuran; hexane / 0.17 h / 20 °C 7.1: 99 percent / TBAF / tetrahydrofuran / 0.17 h / 0 °C 8.1: 74 percent / Et₃N / CH₂Cl₂ / 0.17 h / 20 °C

Reference： [1]Chackalamannil, Samuel; Xia, Yan; Greenlee, William J.; Clasby, Martin; Doller, Darìo; Tsai, Hsingan; Asberom, Theodros; Czarniecki, Michael; Ahn, Ho-Sam; Boykow, George; Foster, Carolyn; Agans-Fantuzzi, Jacqueline; Bryant, Matthew; Lau, Janice; Chintala, Madhu [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 5884 - 5887]

49
[ 1552-91-6 ]
[ 56453-88-4 ]

Reference： [1]Chemische Berichte,1986,vol. 119,p. 2848 - 2858

50
[ 75567-08-7 ]
[ 56453-88-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With water; sodium hydroxide In ethanol at 20℃; for 12h;	17 4.2.17 (E)-3-(Cyclohex-1-en-1-yl)acrylic Acid (trans-21) The hydrolysis of (E)-ethyl 3-(cyclohex-1-en-1-yl)acrylate, using the procedure described above, afforded trans-21 (quant.) as colorless needles: mp 116-117 °C (CH2Cl2/hexane, 5:95); 1H NMR (CDCl3, 400 MHz) δ: 1.54-1.75 (m, 4H, c-Hexene-H), 2.14-2.25 (m, 4H, c-Hexene-H), 5.77 (d, J = 16.4 Hz, 1H, =CH-CO2-), 6.23 (m, 1H, c-Hexene-H), 7.36 (d, J = 16.4 Hz, 1H, c-Hexene-CH=); 13C NMR(CDCl3, 100 MHz) δ: 21.9 (t, c-Hexene), 22.0 (t, c-Hexene), 24.1 (t, c-Hexene), 26.5 (t, c-Hexene), 113.7 (d, =CH-CO2-), 134.9 (s, c-Hexene), 140.3 (d, c-Hexene-CH=), 150.4 (d, c-Hexene), 173.3 (s, C=O); IR (KBr) 1684 cm-1; FAB-MS m/z 152 (M+); Anal. calcd for C10H11O2: C, 71.03; H, 7.95. Found: C, 70.94; H, 7.93; The spectroscopic data were in agreement with those in the literature. (Chackalamannil et al., 1999).

Reference： [1]Abe, Masato; Nishikawa, Keisuke; Okuda, Katsuhiro; Shindo, Mitsuru; Fukuda, Hiroshi; Nakanishi, Kazunari; Tazawa, Yuta; Taniguchi, Tomoya; Park, So-Young; Hiradate, Syuntaro; Fujii, Yoshiharu [Phytochemistry, 2012, vol. 84, p. 56 - 67,12]

51
[ 27944-89-4 ]
[ 56453-88-4 ]
[ 85437-89-4 ]

Yield	Reaction Conditions	Operation in experiment
76 % de	Stage #1: 3-(cyclohex-1-en-1-yl)propiolic acid With 18-crown-6 ether; caesium carbonate In toluene at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: With bis(pinacol)diborane In toluene at 65℃; for 18h; Inert atmosphere; Schlenk technique; Overall yield = 46 %; regioselective reaction;	4.1.13 General procedure for the synthesis of acrylic acid derivatives General procedure: To a solution of alkynoic acid (1 equiv) in toluene at room temperature was added Cs2CO3 (1.2 equiv) and 18-crown-6 (1.2 equiv), and the resulting reaction mixture was stirred for 30min. Subsequently, B2pin2 (1.5 equiv) was added to the solution and the reaction mixture was stirred for additional 16-29hat the indicated temperature. The reaction was quenched with 0.33M hydrochloric acid and extracted with ethyl acetate. The combined organic extracts were washed with brine and dried over sodium sulfate. The solution was filtered and concentrated in vacuo. The residue was purified by silica gel chromatography using a 2:98 ethyl acetate in hexane with 1% acetic acid isocratic method to yield the desired product. Only the trans (major) product are reported, which match the literature values.

Reference： [1]Verma, Astha; Grams, R. Justin; Rastatter, Brett P.; Santos, Webster L. [Tetrahedron, 2019, vol. 75, # 14, p. 2113 - 2117]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	56453-88-4	MDL No. :	N/A
Formula :	C₉H₁₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HTBJZZUJRAWYLX-VOTSOKGWSA-N
M.W :	152.19	Pubchem ID :	5358361
Synonyms :

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.44
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.09
TPSA :	37.3 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.83 cm/s

Log Po/w (iLOGP) :	1.81
Log Po/w (XLOGP3) :	1.97
Log Po/w (WLOGP) :	2.13
Log Po/w (MLOGP) :	1.68
Log Po/w (SILICOS-IT) :	1.79
Consensus Log Po/w :	1.88

[ CAS No. 56453-88-4 ] {[proInfo.proName]}

Quality Control of [ 56453-88-4 ]

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Product Details of [ 56453-88-4 ]

Calculated chemistry of [ 56453-88-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 56453-88-4 ]

Application In Synthesis of [ 56453-88-4 ]

[ 56453-88-4 ] Synthesis Path-Downstream 1~51

Related Functional Groups of
[ 56453-88-4 ]

Alkenes

Aliphatic Cyclic Hydrocarbons

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.85

Log S (ESOL) :	-1.89
Solubility :	1.95 mg/ml ; 0.0128 mol/l
Class :	Very soluble
Log S (Ali) :	-2.38
Solubility :	0.636 mg/ml ; 0.00418 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.74
Solubility :	27.4 mg/ml ; 0.18 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.98

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:	N/A
Hazard Statements:	H302-H312-H332	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 56453-88-4 ] {[proInfo.proName]}

Quality Control of [ 56453-88-4 ]

Related Doc. of [ 56453-88-4 ]

Product Details of [ 56453-88-4 ]

Calculated chemistry of [ 56453-88-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 56453-88-4 ]

Application In Synthesis of [ 56453-88-4 ]

[ 56453-88-4 ] Synthesis Path-Downstream 1~51

Related Functional Groups of [ 56453-88-4 ]

Alkenes

Aliphatic Cyclic Hydrocarbons

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 56453-88-4 ]