[ CAS No. 546-43-0 ] {[proInfo.proName]}

Name: 546-43-0|(3aR,5S,8aR,9aR)-5,8a-Dimethyl-3-methylene-3,3a,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(5H)-one|98%
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SKU: A354359
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2D 3D

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Quality Control of [ 546-43-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 546-43-0 ]

SDS Specification

Alternatived Products of [ 546-43-0 ]

Product Details of [ 546-43-0 ]

CAS No. :	546-43-0	MDL No. :
Formula :	C₁₅H₂₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	232.32	Pubchem ID :	-
Synonyms :	Alant camphor;Inula camphor;AI3-31147;NSC 93131;NSC 333843;helenine;helenin;(+)-Alantolactone	Chemical Name :	(3aR,5S,8aR,9aR)-5,8a-Dimethyl-3-methylene-3,3a,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(5H)-one

Calculated chemistry of [ 546-43-0 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	67.95
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.71
Log Po/w (XLOGP3) :	3.38
Log Po/w (WLOGP) :	3.24
Log Po/w (MLOGP) :	3.35
Log Po/w (SILICOS-IT) :	3.25
Consensus Log Po/w :	3.19

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.41
Solubility :	0.0904 mg/ml ; 0.000389 mol/l
Class :	Soluble
Log S (Ali) :	-3.61
Solubility :	0.0569 mg/ml ; 0.000245 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.05
Solubility :	0.206 mg/ml ; 0.000885 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.19

Safety of [ 546-43-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280	UN#:	N/A
Hazard Statements:	H317	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 546-43-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 546-43-0 ]

[ 546-43-0 ] Synthesis Path-Downstream 1~88

1
[ 546-43-0 ]
[ 40285-97-0 ]
[ 58526-58-2 ]

Reference： [1]Helvetica Chimica Acta,1931,vol. 14,p. 397,405
[2]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1958,vol. 246,p. 1874

2
[ 129119-12-6 ]
[ 546-43-0 ]
[ 129119-13-7 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 107 - 115

3
[ 546-43-0 ]
[ 107439-71-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With Perbenzoic acid; In dichloromethane; at 20℃; for 3h;	<strong>[546-43-0]Alantolactone</strong> (2.0g, 8.6mmol) was dissolved in dichloromethane (10mL),To the above system was slowly added dropwise a solution of peroxybenzoic acid (2.1 g, 10.3 mmol) in dichloromethane (20 mL)Reaction at room temperature for 3 hours,Saturated aqueous sodium thiosulfate solution was quenched,The organic layer was washed with saturated aqueous sodium bicarbonate (20 mL x 3)Dry and concentrate,Purification by column chromatography (petroleum ether: ethyl acetate = 5: 2) gave Compound (I-III) (White solid, 2.0 g, yield 94%)
94%	With Perbenzoic acid; In dichloromethane; at 20℃; for 3h;	<strong>[546-43-0]Alantolactone</strong> (2.0g, 8.6mmol) was dissolved in dichloromethane (10mL),To the above system was slowly added dropwise a solution of peroxybenzoic acid (2.1 g, 10.3 mmol) in dichloromethane (20 mL)Reaction at room temperature for 3 hours,Saturated aqueous sodium thiosulfate solution was quenched,The organic layer was washed with saturated aqueous sodium bicarbonate (20 mL x 3)Dry and concentrate,Purification by column chromatography (petroleum ether: ethyl acetate = 5: 2) gave Compound (I-III) (White solid, 2.0 g, yield 94%)
94%	With Perbenzoic acid; In dichloromethane; at 20℃; for 3h;	<strong>[546-43-0]Alantolactone</strong> (2.0 g, 8.6 mmol) was dissolved in dichloromethane (10 mL).Slowly add peroxybenzoic acid (2.1 g, 10.3 mmol) to the above systema solution of dichloromethane (20 mL),Reaction at room temperature for 3 hours,Saturated aqueous sodium thiosulfate quenches the reaction,Organic layer saturatedWash with aqueous sodium bicarbonate solution (20 mL × 3),Dry and concentrated,Purification by column chromatography (petroleum ether:ethyl acetate=5:2) to give compound (I-III)(white solid, 2.0 g, yield 94%)

90%

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 3h;

<strong>[546-43-0]Alantolactone</strong>(2.0 g, 8.6 mmol) was dissolved in CH2Cl2 (10 mL). m-CPBA(2.1 g, 10 mmol) in dichloromethane (10 mL) was added dropwiseto this solution. The mixture was stirred at room temperature for3 h. Then the reaction mixture was diluted with 30 mL saturatedNa2S2O3 solution, washed with saturated NaHCO3 solution, driedover anhydrous Na2SO4, filtered, and evaporated to afford a crudeproduct, which was purified by column chromatography [petroleumetherEtOAc (5:2)] to obtain compound 3 as a white solid(1.9 g, 90%). mp 164-166 C. 1H NMR (400 MHz, CDCl3) delta (ppm) 6.40(s, 1H), 5.77 (s, 1H), 4.78e4.55 (m, 1H), 3.66 (dt, J 8.9, 2.8 Hz, 1H),2.89 (d, J 2.5 Hz, 1H), 1.92-1.64 (m, 3H), 1.59-1.28 (m, 6H), 1.11 (s,3H), 1.04 (dd, J 7.8, 2.1 Hz, 3H). 13C NMR (100 MHz, CDCl3) delta (ppm)169.5, 136.6, 123.6, 75.0, 67.4, 61.1, 39.4, 37.6, 37.3, 37.0, 32.5, 29.4,23.8, 18.0, 16.4. HR-MS (ESI) m/z: calcd for C15H20O3Na [M Na]271.1305, found 271.1306.

Reference： [1]Chemistry of Natural Compounds,2006,vol. 42,p. 400 - 406
[2]Patent: CN106491593,2017,A .Location in patent: Paragraph 0029; 0032; 0033; 0034
[3]Patent: CN106491592,2017,A .Location in patent: Paragraph 0028; 0031; 0032; 0033
[4]Patent: CN106496169,2017,A .Location in patent: Paragraph 0033; 0034; 0035
[5]European Journal of Medicinal Chemistry,2018,vol. 157,p. 229 - 247
[6]Chemistry of Natural Compounds,1996,vol. 32,p. 869 - 872
[7]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1985,vol. 24,p. 835 - 839
[8]Phytochemistry,1982,vol. 21,p. 1679 - 1692
[9]Phytochemistry,1988,vol. 27,p. 2079 - 2082
[10]Planta Medica,1999,vol. 65,p. 351 - 355
[11]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697
[12]Molecules,2013,vol. 18,p. 13061 - 13077

4
[ 546-43-0 ]
[ 126686-70-2 ]
alantolactone-Cys(Boc)-Ala(OMe) adduct [ No CAS ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 5029 - 5038

5
[ 546-43-0 ]
[ 126686-70-2 ]
alantolactone-Cys(Boc)-Ala(OMe) adduct [ No CAS ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 5029 - 5038

6
[ 930-69-8 ]
[ 546-43-0 ]
[ 123489-73-6 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 6106 - 6113

7
[ 546-43-0 ]
[ 65563-77-1 ]

Reference： [1]Chemistry of Natural Compounds,2006,vol. 42,p. 400 - 406

8
[ 546-43-0 ]
[ 86918-97-0 ]

Reference： [1]Chemistry of Natural Compounds,2006,vol. 42,p. 400 - 406

9
[ 546-43-0 ]
(3aR,5S,8aR,9aR)-3-Benzenesulfinylmethyl-5,8a-dimethyl-3a,5,6,7,8,8a,9,9a-octahydro-3H-naphtho[2,3-b]furan-2-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 6106 - 6113

10
[ 546-43-0 ]
[ 123538-94-3 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 6106 - 6113

11
[ 546-43-0 ]
[ 123538-98-7 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 6106 - 6113

12
[ 5460-32-2 ]
[ 546-43-0 ]
[ 1192803-35-2 ]
[ 1192803-36-3 ]

Reference： [1]Doklady Chemistry,2009,vol. 426,p. 138 - 142

13
[ 123-75-1 ]
[ 546-43-0 ]
[ 447458-26-6 ]

Reference： [1]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697
[2]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2715 - 2721

14
[ 110-89-4 ]
[ 546-43-0 ]
[ 1245718-95-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2715 - 2721
[2]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697

15
[ 4556-23-4 ]
[ 546-43-0 ]
[ 1245719-02-1 ]

Reference： [1]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697

16
[ 107-10-8 ]
[ 546-43-0 ]
[ 1245719-03-2 ]

Reference： [1]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697

17
[ 124-22-1 ]
[ 546-43-0 ]
[ 1245719-13-4 ]

Reference： [1]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697

18
[ 111-26-2 ]
[ 546-43-0 ]
[ 1245719-06-5 ]

Reference： [1]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697

19
[ 112-20-9 ]
[ 546-43-0 ]
[ 1245718-97-1 ]

Reference： [1]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697

20
[ 2016-57-1 ]
[ 546-43-0 ]
[ 1245719-09-8 ]

Reference： [1]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697

21
[ 7307-55-3 ]
[ 546-43-0 ]
[ 1245719-11-2 ]

Reference： [1]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697

22
[ 39191-07-6 ]
[ 546-43-0 ]
[ 1245719-00-9 ]

Reference： [1]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697

23
[ 546-43-0 ]
[ 109-89-7 ]
[ 1245718-93-7 ]

Reference： [1]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697

24
[ 546-43-0 ]
[ 109-73-9 ]
[ 956931-62-7 ]

Reference： [1]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697

25
[ 546-43-0 ]
[ 100-46-9 ]
[ 447458-64-2 ]

Reference： [1]Chemistry and biodiversity,2010,vol. 7,p. 1681 - 1697

26
[ 61-54-1 ]
[ 546-43-0 ]
[ 1353868-56-0 ]

Reference： [1]Chemistry of Natural Compounds,2011,vol. 47,p. 716 - 725

27
[ 61-54-1 ]
[ 546-43-0 ]
[ 1353868-71-9 ]

Reference： [1]Chemistry of Natural Compounds,2011,vol. 47,p. 716 - 725

28
[ 608-07-1 ]
[ 546-43-0 ]
[ 1353868-57-1 ]

Reference： [1]Chemistry of Natural Compounds,2011,vol. 47,p. 716 - 725

29
[ 546-43-0 ]
(3aR,5S,8aR,9aR)-3-[(2-hydroxy-1-methyl-2-phenylethyl)methylamino]methyl}-5,8a-dimethyl-4,4a-epoxy-decahydronaphtho[2,3-b]furan-2-one [ No CAS ]

Reference： [1]Chemistry of Natural Compounds,2011,vol. 47,p. 716 - 725

30
[ 546-43-0 ]
C₁₅H₂₀O₃ [ No CAS ]

Reference： [1]Chemistry of Natural Compounds,2011,vol. 47,p. 716 - 725

31
[ 546-43-0 ]
[ 485-35-8 ]
[ 1353868-59-3 ]

Reference： [1]Chemistry of Natural Compounds,2011,vol. 47,p. 716 - 725

32
[ 546-43-0 ]
[ 493-48-1 ]
(3aR,5S,8aR,9aR)-3-((6,7-dimethoxy-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-5,8a-dimethyl-3,3a,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(5H)-one [ No CAS ]

Reference： [1]Chemistry of Natural Compounds,2011,vol. 47,p. 716 - 725

33
[ 546-43-0 ]
[ 299-42-3 ]
(3aR,5S,8aR,9aR)-3-(((1-hydroxy-1-phenylpropan-2-yl)(methyl)amino)methyl)-5,8a-dimethyl-3,3a,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(5H)-one [ No CAS ]

Reference： [1]Chemistry of Natural Compounds,2011,vol. 47,p. 716 - 725

34
[ 1126-09-6 ]
[ 546-43-0 ]
[ 1401324-87-5 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2012,vol. 48,p. 698 - 703,6

35
[ 1117-96-0 ]
[ 546-43-0 ]
[ 1443156-49-7 ]

Reference： [1]Journal of Chemical Sciences,2013,vol. 125,p. 187 - 191

36
[ 764-02-3 ]
[ 546-43-0 ]
C₁₈H₂₆N₂O₂ [ No CAS ]

Reference： [1]Journal of Chemical Sciences,2013,vol. 125,p. 187 - 191

37
[ 186581-53-3 ]
[ 546-43-0 ]
[ 91379-32-7 ]

Reference： [1]Journal of Chemical Sciences,2013,vol. 125,p. 187 - 191

38
[ 10575-90-3 ]
[ 546-43-0 ]
[ 1415894-15-3 ]

Reference： [1]Russian Chemical Bulletin,2012,vol. 61,p. 280 - 286
Izv. Akad. Nauk, Ser. Khim.,2012,vol. 61,p. 280 - 286,7

39
[ 696-62-8 ]
[ 546-43-0 ]
(3aR,5S,8aR,9aR,E)-3-(4-methoxybenzylidene)-5,8a-dimethyl-3,3a,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(5H)-one [ No CAS ]
(5S,8aR,9aS)-3-(4-methoxybenzyl)-5,8a-dimethyl-6,7,8,8a,9,9a-hexahydronaphtho[2,3-b]furan-2(5H)-one [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2012,vol. 61,p. 1975 - 1985
Izv. Akad. Nauk, Ser. Khim.,2012,vol. 61,p. 1959 - 1968,11

40
[ 20469-63-0 ]
[ 546-43-0 ]
(3aR,5S,8aR,9aR,E)-3-(2,4-dimethoxybenzylidene)-5,8a-dimethyl-3,3a,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(5H)-one [ No CAS ]
(5S,8aR,9aS)-3-(2,4-dimethoxybenzyl)-5,8a-dimethyl-6,7,8,8a,9,9a-hexahydronaphtho[2,3-b]furan-2(5H)-one [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2012,vol. 61,p. 1975 - 1985
Izv. Akad. Nauk, Ser. Khim.,2012,vol. 61,p. 1959 - 1968,11

41
[ 3058-39-7 ]
[ 546-43-0 ]
(5S,8aR,9aS)-3,5,8a-trimethyl-6,7,8,8a,9,9a-hexahydronaphtho[2,3-b]furan-2(5H)-one [ No CAS ]
(5S,8aR,9aS)-3-(4-cyanobenzyl)-5,8a-dimethyl-6,7,8,8a,9,9a-hexahydronaphtho[2,3-b]furan-2(5H)-one [ No CAS ]
4-{(2S,3S,3a'R,5R,5S',8aS,8a'R,9aR,9a'R)-5,5',8a,8a'-tetramethyl-2'-oxo-3,3a',5,5',6,6',7,7',8,8a,8',8a',9,9a,9',9a'-hexadecahydro-1H,2'H-spiro[anthracene-2,3'-naphtho[2,3-b]furan]-3-yl}benzonitrile [ No CAS ]
(3aR,5S,8aR,9aR,E)-3-(4-cyanobenzylidene)-5,8a-dimethyl-3,3a,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(5H)-one [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2012,vol. 61,p. 1975 - 1985
Izv. Akad. Nauk, Ser. Khim.,2012,vol. 61,p. 1959 - 1968,11

42
[ 352-34-1 ]
[ 546-43-0 ]
(3aR,5S,8aR,9aR,E)-3-(4-fluorobenzylidene)-5,8a-dimethyl-3,3a,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(5H)-one [ No CAS ]
(5S,8aR,9aS)-3-(4-fluorobenzyl)-5,8a-dimethyl-6,7,8,8a,9,9a-hexahydronaphtho[2,3-b]furan-2(5H)-one [ No CAS ]
(5S,8aR,9aS)-3,5,8a-trimethyl-6,7,8,8a,9,9a-hexahydronaphtho[2,3-b]furan-2(5H)-one [ No CAS ]
(2S,3S,3a'R,5R,5'S,8aS,8a'R,9aR,9a'R)-3-(4-fluorophenyl)-5,5',8a,8a'-tetramethyl-3,3a',5,5',6,6',7,7',8,8a,8',8a',9,9a,9',9a'-hexadecahydro-1H,2'H-spiro[anthracene-2,3'-naphtho[2,3-b]furan]-2'-one [ No CAS ]

Reference： [1]Russian Chemical Bulletin,2012,vol. 61,p. 1975 - 1985
Izv. Akad. Nauk, Ser. Khim.,2012,vol. 61,p. 1959 - 1968,11

43
[ 20830-81-3 ]
[ 546-43-0 ]
C₄₂H₄₉NO₁₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	In methanol;	<strong>[546-43-0]Alantolactone</strong> (100 mg, 0.431 mmol) was dissolved in MeOH (3 mL) and treated with daunorubicinbase (250 mg, 0.474 mmol). The course of the reaction was monitored by TLC on Silufol plates using CHCl3-MeOH (4:1,Rf of 3a, 0.77). When the reaction was finished, the mixture was evaporated at reduced pressure. The residue was rinsed withMeOH and purified by column chromatography over silica gel (15 g) with elution first by CHCl3 and then by a mixture with 20% MeOH. Evaporation afforded the product (157 mg, 48%, 0.207 mmol) as red plate-like crystals, mp 152-158, found:m/z 760.3290 [ + H]+. C42H49NO12. Calcd: 760.3328 [M + H]+. 1 NMR spectrum (CDCl3, , ppm, J/Hz): 1.07 (3H, d,J = 8.4, H-42), 1.10 (1H, m, H-34), 1.19 (3H, s, H-41), 1.36 (3H, d, J = 6.6, H-27), 1.41 (1H, m, H-35), 1.46 (1H, br.s,H-32), 1.49 (2H, br.t, H-36), 1.57 (1H, d, J = 11.7, H-34), 1.74 (3H, m, H-23 + H-35), 2.09 (2H, td, J1 = 14.4, J2 = 3.7,H-32 + H-12), 2.37 (1H, dt, J1 = 14.8, J2 = 1.8, H-12), 2.42 (4H, m, H-20 + H-37), 2.77 (1H, m, H-28), 2.90 (3H, m,H-24 + H-28 + H-29), 2.94 (1H, d, J = 18.8, H-10), 3.08 (1H, ddd, J1 = 8.2, J2 = 5.6, J1 = 3.1, H-30), 3.21 (1H, dd, J1 = 18.8,J2 = 1.8, H-10), 3.65 (1H, br.s, H-25), 4.07 (4H, m, H-21 + H-26), 4.70 (1H, dt, J1 = 5.6, J2 = 2.5, H-31), 5.04 (1H, d, J = 3.1,H-39), 5.28 (1H, dd, J1 = 3.7, J2 = 1.8, H-13), 5.51 (1H, d, J = 3.2, H-22), 7.38 (1H, d, J = 8.1, H-2), 7.77 (1H, t, J = 8.1, H-3),8.01 (1H, d, J = 8.1, H-4). 13C NMR spectrum (CDCl3, , ppm): 16.8 (C-35), 17.1 (C-27), 22.9 (C-42), 24.8 (C-20), 28.6(C-41), 30.3 (C-23), 32.8 (C-36), 33.0 (C-10), 33.3 (C-33), 34.9 (C-12), 37.8 (C-30), 38.5 (C-37), 42.3 (C-34 + C-28), 42.7(C-32), 45.8 (C-29), 52.3 (C-24), 56.7 (C-21), 66.8 (C-26), 67.1 (C-25), 69.9 (C-13), 76.9 (C-31), 101.1 (C-22), 114.5 (C-39),118.4 (C-2), 119.8 (C-4), 121.0 (C-18), 135.7 (C-3), 151.5 (C-38), 155.9 (C-8), 156.5 (C-15), 161.1 (C-1), 186.7 (C-6), 187.0(C-17), 177.7 (C-40), 211.8 (C-19).
48%	In methanol; chloroform; at 20℃; for 168h;	General procedure: The corresponding lactone (I)-(VI)(0.431 mmol) was dissolved in the mixture of methanol(1.5 mL) and chloroform (1.5 mL). Daunorubicin(250 mg) was added as a free amine. The reaction mixturewas kept seven days at room temperature. Thereaction was monitored by TLC in the CHCl3-MeOHchromatographic system (9 : 1). The product Rf ? 0.5.The reaction mixture was evaporated at a reducedpressure and purified by column chromatography onsilica gel. The column was first eluted with CHCl3 tothe total removal of the low-polar colored daunorubicinaglycon and with the mixture of chloroform with20% methanol. The colored product was eluted from the column as a narrow zone, and the unreacteddaunorubicin remained at the column start.

Reference： [1]Chemistry of Natural Compounds,2016,vol. 52,p. 695 - 696
Khim. Prir. Soedin.,2016,p. 597 - 598,2
[2]Russian Journal of Bioorganic Chemistry,2018,vol. 44,p. 538 - 546
Bioorg. Khim.,2018,vol. 44,p. 538 - 546,9

44
[ 25316-40-9 ]
[ 546-43-0 ]
C₄₂H₄₉NO₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With sodium hydrogencarbonate; In methanol; water; at 20℃; for 144h;	Doxorubicin hydrochloride (250 mg, 0.431 mmol), <strong>[546-43-0]alantolactone</strong> (2, 100.1 mg, 0.431 mmol), andNaHCO3 (72 mg, 0.862 mmol) were dissolved in MeOH (3 mL) and H2O (0.1 mL) and left for 6 d at room temperature. Thecourse of the reaction was monitored by TLC on Silufol plates using CHCl3-MeOH (4:1, Rf of 3b, 0.75). The mixture wasevaporated at reduced pressure and purified by column chromatography over silica gel (20 g) with elution first by CHCl3 andthen by mixtures with added MeOH (10% and 20%). Evaporation afforded the product (144 mg, 43%, 0.186 mmol) as redplate-like crystals, mp 214-220, found: m/z 776.3244 [ + H]+. C42H49NO13. Calcd: 776.3277 [M + H]+. 1 NMR spectrum(CDCl3, , ppm, J/Hz): 0.90 (3H, d, J = 7.4, H-42), 0.9 (1, m, H-34), 1.00 (3H, s, H-41), 1.15 (3H, d, J = 6.5, H-27), 1.21 (1H,m, H-35), 1.32 (2H, m, H-32 + H-36), 1.40 (1H, m, H-34), 1.63 (3H, m, H-23 + H-35), 1.89 (1H, dd, J1 = 14.8, J2 = 2.9,H-32), 1.98 (1H, dd, J1 = 14.9, J2 = 4.2, H-12), 2.20 (1H, d, J = 14.9, H-12), 2.24 (1H, m, H-37), 2.54 (1H, m, H-28), 2.69(1H, m, H-24), 2.79 (3H, m, H-10 + H-28 + H-29), 2.96 (1H, m, H-30), 3.02 (1H, d, J = 18.0, H-10), 3.52 (1H, br.s, H-25),3.89 (4H, m, H-21 + H-26), 4.59 (3H, m, H-20 + H-31), 4.89 (1H, d, J = 2.5, H-39), 5.07 (1H, br.s, H-13), 5.32 (1H, br.s,H-22), 7.26 (1H, m, H-2), 7.62 (1H, t, J = 8.2, H-3), 7.80 (1H, d, J = 8.2, H-4). 13C NMR spectrum (CDCl3, , ppm): 16.5(C-35), 16.6 (C-27), 22.6 (C-42), 28.3 (C-41), 30.0 (C-23), 32.6 (C-36), 32.8 (C-33), 33.4 (C-10), 35.4 (C-12), 37.5 (C-30),38.3 (C-37), 42.0 (C-34), 42.1 (C-28), 42.4 (C-32), 45.7 (C-29), 52.7 (C-24), 56.4 (C-21), 64.9 (C-20), 66.8 (C-25), 67.3(C-26), 69.5 (C-13), 77.3 (C-31), 100.9 (C-22), 114.4 (C-39), 118.6 (C-2), 119.6 (C-4), 135.8 (C-3).
43%	With triethylamine; In methanol; chloroform; at 20℃; for 168h;	General procedure: The corresponding lactone (I)-(VI)(0.431 mmol) was dissolved in the mixture of methanol(1.5 mL) and chloroform (1.5 mL). Doxorubicinhydrochloride (250 mg) and triethylamine (120 muL,2 equivalents) were added. The reaction mixture waskept seven days at room temperature. The reaction wasmonitored by TLC in the CHCl3-MeOH chromatographicsystem (9 : 1). The product Rf ? 0.5. The reactionmixture was evaporated at a reduced pressure andpurified by column chromatography on silica gel. Thecolumn was eluted with CHCl3 and then with 20%MeOH in chloroform. The product was eluted fromthe column as a narrow zone.

45
[ 546-43-0 ]
[ 40285-97-0 ]

Yield	Reaction Conditions	Operation in experiment
1.8 g	With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; for 0.25h;	<strong>[546-43-0]Alantolactone</strong>, 1 (2.0g) was dissolved in dry THF (20.0mL) and lithium tri-tert-butoxyaluminohydride (1.0 g) was added. The reaction mixture was stirred for 15 min, the progress of reaction was monitored by TLC. After completion of reaction, THF was removed under vacuum and few drops of glacial acetic acid were added and the reaction mixture was extracted with water and finally with diethyl ether (3 × 50 mL). Evaporation of solvent afforded pure crystals of dihydro<strong>[546-43-0]alantolactone</strong> (7, 1.8 g). Iso<strong>[546-43-0]alantolactone</strong> give dihydroiso<strong>[546-43-0]alantolactone</strong> (8, 1.9 g) under similar reaction conditions.

Reference： [1]Asian Journal of Chemistry,2017,vol. 29,p. 568 - 570

46
[ 67-56-1 ]
[ 546-43-0 ]
13-methoxydihydroalantolactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.34 g	With magnesium; for 3h;	To dry methanol (50 mL), <strong>[546-43-0]alantolactone</strong> (0.5 g) and active Mg turnings (0.5 g) were added with constant stirring under dry conditions. A mild exothermic reaction was observed after 3 h with the evolution of hydrogen gas. Unreacted metal was then separated and the mixture was added to dilute HCl (150 mL) to get clear solution. The pH was adjusted around 8-9 by adding ammonia solution. The reaction mixture was then diluted with water and extracted with dichloromethane (4 × 20 mL). The organic layer was dried (anhydrous sodium sulfate) and evaporation of solvent under vacuum afforded a mixture (0.44 g) which on chromatography over silica gel yielded pure compound 13-methoxydihydro<strong>[546-43-0]alantolactone</strong> (3, 0.34 g) with m.p. 82 C. Iso<strong>[546-43-0]alantolactone</strong> was subjected to reaction using same method to yield13-methoxydihydroiso<strong>[546-43-0]alantolactone</strong> (4, 1.6 g) with m.p.91 C.

Reference： [1]Asian Journal of Chemistry,2017,vol. 29,p. 568 - 570

47
[ 75-25-2 ]
[ 546-43-0 ]
C₁₆H₂₀Br₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.9 g	With N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide; In water; at 20℃; for 5h;	CHBr3 (15 mL) was treated with aqueous KOH (10 mL, 50 %) and phase transfer catalyst (TEBAC,100 mg), stirred and treated with <strong>[546-43-0]alantolactone</strong> (2,1.0 g). Stirring was continued at room temperature for 5 h. The reaction mixture was diluted with water and extracted with ethyl acetate (3× 50 mL) and dried over anhydrous sodium sulfate. Solvent was removed under vacuum. The crystalline pure compound (5, 0.9 g) was obtained having m.p.58 C. Iso<strong>[546-43-0]alantolactone</strong> on reaction with bromoform (CHBr3) under similar reaction conditions afforded a product (6, 0.8 g) with m.p. 149 C.

Reference： [1]Asian Journal of Chemistry,2017,vol. 29,p. 568 - 570

48
[ 546-43-0 ]
K⁽¹⁺⁾*C₁₅H₂₁O₃^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In water;	A solution of KOH (360 mg) in H2O (10 mL) was treated with <strong>[546-43-0]alantolactone</strong> (1, 500 mg,2.15 mmol). The solution was stirred and became completely transparent when 1 was hydrolyzed to the potassium salt. A stream of CO2 was passed through the reaction mixture until the pH was close to neutral. Crystals of I2 (1365 mg,5.375 mmol) and KI (100 mg) to improve the solubility were added to the solution, which was left at room temperature for3 d, transferred to a separatory funnel, diluted with H2O and CHCl3, treated in small portions with crystals of sodium thiosulfatehydrate to eliminate the strong brown iodine color, and extracted (2) with CHCl3. The organic fractions were evaporated.The residue was chromatographed over a column of silica gel (10 g) with elution first by C6H6 and then C6H6-EtOAc (2:1).The major uncolored fraction was 2 with Rf 0.63 (C6H6-EtOAc, 4:1) on Silufol.

Reference： [1]Chemistry of Natural Compounds,2016,vol. 52,p. 943 - 944
Khim. Prir. Soedin.,2016,vol. 52,p. 807 - 808,2

49
[ 10381-82-5 ]
[ 546-43-0 ]
8-(((5S,8aR,9aS)-5,8a-dimethyl-2-oxo-2,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-3-yl)methyl)-1,3,7-trimethyl-1H-purine-2,6(3H,7H)dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With tetrabutylammomium bromide; palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 140℃; for 40h;Inert atmosphere; Molecular sieve; Sealed tube;	General procedure: A glass ampoule was charged under argon with methylenelactone (1.0 mmol), 8-bromoxanthine (1.2 mmol), Pd(OAc)2 (9 mg,0.04 mmol, 4 mol %), NEt3 (152 mg, 1.5 mmol), DMF (5 mL), 3 molecular sieves (3 mg), and appropriate ligand (16 mol %), as wellas TBAB (1.0 mmol) when needed. The ampoule was sealed andheated under the conditions given in Tables 1 and 2 When the re-action was complete, the ampoule was cooled, opened, the mixturewas ltrated, the ltrate was poured into a saturated NaCl solution(20 mL) and extracted with EtOAc (4 10 mL). The combined or-ganics extracts were dried over MgSO4, ltered and concentratedunder reduced pressure. The oily residue was dissolved in CHCl3and separated by silica gel coloumn chromatography (eluentCHCl3eEtOH, gradient 100:1 / 100:4). The starting lactone waseluted rst (in the case of incomplated conversion), followed byexo-, endo-compounds, and xanthenes.

Reference： [1]Tetrahedron,2017,vol. 73,p. 2717 - 2726

50
[ 506-59-2 ]
[ 546-43-0 ]
C₁₇H₂₇NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium carbonate; In dichloromethane; for 3h;Reflux;	The citrus lactone (300.0 mg, 1.29 mmol) was dissolved in dichloromethane (50 mL)Dimethylamine hydrochloride (1.6 g, 19.4 mmol) and potassium carbonate (5.2 g, 37.4 mmol) were added to the above-mentioned mixed system, and the reaction was heated under reflux for 3 hours.The solid was removed by filtration,The filtrate was washed with water, dried and concentrated, and purified by column chromatography (petroleum ether:Ethyl acetate = 1: 1) to give the compound (I-II) (white solid, 236.0 g, yield: 50%).
50%	With potassium carbonate; In dichloromethane; for 3h;Reflux;	<strong>[546-43-0]Alantolactone</strong> (300.0mg, 1.29mmol) was dissolved in dichloromethane (50mL),To the above mixture was added dimethylamine hydrochloride (1.6 g, 19.4 mmol)And potassium carbonate (5.2 g, 37.4 mmol),The system was heated to reflux for 3 hours,Filter to remove the solid,The filtrate was washed with water,Dry and concentrate,Purification by column chromatography (petroleum ether: ethyl acetate = 1: 1) gave Compound (I-II)(White solid, 236.0 g, yield: 50%).
50%	With potassium carbonate; In dichloromethane; for 3h;Reflux;	<strong>[546-43-0]Alantolactone</strong> (300.0mg, 1.29mmol) was dissolved in dichloromethane (50mL),To the above mixture was added dimethylamine hydrochloride (1.6 g, 19.4 mmol)And potassium carbonate (5.2 g, 37.4 mmol),The system was heated to reflux for 3 hours,Filter to remove the solid,The filtrate was washed with water,Dry and concentrate,Purification by column chromatography (petroleum ether: ethyl acetate = 1: 1) gave Compound (I-II)(White solid, 236.0 g, yield: 50%).

50%

With potassium carbonate; In dichloromethane; for 3h;Reflux;

<strong>[546-43-0]Alantolactone</strong> (300.0 mg, 1.29 mmol) was dissolved in dichloromethane (50 mL),Dimethylamine hydrochloride (1.6 g, 19.4 mmol) was added to the above mixed system in order andPotassium carbonate (5.2 g, 37.4 mmol) was heated at reflux for 3 hours.The solid was removed by filtration and the filtrate was washed with water, dried and concentrated.Purification by column chromatography (petroleum ether: ethyl acetate = 1:1) gives compound (I-II)(White solid, 236.0 g, yield: 50%).

Reference： [1]Patent: CN106491594,2017,A .Location in patent: Paragraph 0024; 0025; 0026
[2]Patent: CN106491593,2017,A .Location in patent: Paragraph 0020; 0023; 0024; 0025
[3]Patent: CN106491592,2017,A .Location in patent: Paragraph 0019; 0022; 0023; 0024
[4]Patent: CN106496169,2017,A .Location in patent: Paragraph 0024; 0025; 0026

51
[ 506-59-2 ]
[ 546-43-0 ]
[ 110-17-8 ]
C₁₇H₂₇NO₃*C₄H₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.3%		1) Preparation of the compound (I-III)The citrus lactone (2.0 g, 8.6 mmol) was dissolved in dichloromethane (10 mL)A solution of peroxybenzoic acid (2.1 g, 10.3 mmol) in dichloromethane (20 mL) was slowly added dropwise to the above system,Reaction at room temperature for 3 hours,Saturated sodium thiosulfate aqueous solution quenching reaction,The organic layer was washed with saturated aqueous sodium bicarbonate (20 mL x 3)Dried and concentrated,The crude compound (I-III) (white solid, 2.0 g, yield 94%) was purified by column chromatography (petroleum ether: ethyl acetate = 5: 2)2) Preparation of compound (III)The compound (I-III) (300.0 mg, 1.29 mmol) obtained in the above step was dissolved in dichloromethane (50 mL)To the above mixture was added dimethylamine hydrochloride (1.6 g, 19.4 mmol) and potassium carbonate (5.2 g, 37.4 mmol)Heated to reflux for 3 hours,The solid was removed by filtration,The filtrate was washed with water,Dried and concentrated, and the resulting crude product was dissolved in methanol (7 mL)To the above mixed system was added fumaric acid (130.1 mg, 1.11 mmol)The reaction was stirred for 0.5 hour,Remove the solvent,Add ethyl acetate to dissolve,The compound (III) was collected by filtration (white solid, 369.6 mg, yield: 87.3%)Determination of compound (II) by elemental analysis Molecular formula: C22H35NO7

Reference： [1]Patent: CN106491594,2017,A .Location in patent: Paragraph 0033; 0034; 0036; 0037; 0038; 0039

52
[ 546-43-0 ]
C₁₇H₂₇NO₃ [ No CAS ]

Reference： [1]Patent: CN106491592,2017,A

53
[ 546-43-0 ]
C₄H₄O₄*C₁₇H₂₇NO₂ [ No CAS ]

Reference： [1]Patent: CN106491592,2017,A

54
[ 546-43-0 ]
C₁₇H₂₇NO₃*C₄H₄O₄ [ No CAS ]

Reference： [1]Patent: CN106491592,2017,A

55
[ 546-43-0 ]
[ 100-46-9 ]
13-benzylaminoalantolactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92.3%	In methanol; at 0 - 20℃; for 4h;	<strong>[546-43-0]Alantolactone</strong> pure product 233mg was dissolved in 10mL of methanol was stirred at 0 deg.] C, 158mg of benzyl amine was slowly added dropwise, followed by stirring at room temperature for 4 hours. The reaction mixture was concentrated to remove methanol, and the resulting reaction was dissolved with 20mL of ethyl acetate under reduced pressure, and washed with saturated NH4Cl aqueous solution was washed 3 times. Ethyl acetate was removed under reduced pressure and the resulting mixture was concentrated. The mixture was mixed with 0.5g silica gel 200-300 mesh, silica gel (200-300 mesh, 10g) chromatography with ethyl acetate: ethanol (1: 1 by volume) as eluent gradient elution to give 13- benzylamine - <strong>[546-43-0]alantolactone</strong> pure product (313 mg), purity by HPLC 98.5%, yield of 92.3%, significantly higher than the literature (Chemistry & Biodiversity (2010), 7 (7), 1681-1697) 56.7% reported in . The present invention is a reaction system as methanol, saturated with NH4 Washed with an aqueous solution of Cl, greatly improves the purity and yield of the product.

Reference： [1]Patent: CN104663662,2016,B .Location in patent: Paragraph 0026; 0027

56
[ 546-43-0 ]
C₁₇H₂₇NO₃*C₄H₄O₄ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 157,p. 229 - 247

57
[ 771-99-3 ]
[ 546-43-0 ]
C₂₆H₃₅NO₂ [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2715 - 2721

58
[ 110-91-8 ]
[ 546-43-0 ]
[ 1267572-96-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2715 - 2721

59
[ 693-98-1 ]
[ 546-43-0 ]
C₁₉H₂₆N₂O₂ [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2715 - 2721

60
[ 35794-11-7 ]
[ 546-43-0 ]
C₂₂H₃₅NO₂ [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2715 - 2721

61
[ 13889-98-0 ]
[ 546-43-0 ]
C₂₁H₃₂N₂O₃ [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2715 - 2721

62
[ 626-58-4 ]
[ 546-43-0 ]
C₂₁H₃₃NO₂ [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2715 - 2721

63
[ 31252-42-3 ]
[ 546-43-0 ]
C₂₇H₃₇NO₂ [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2715 - 2721

64
[ 50541-93-0 ]
[ 546-43-0 ]
C₂₇H₃₈N₂O₂ [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2715 - 2721

65
[ 288-32-4 ]
[ 546-43-0 ]
C₁₈H₂₄N₂O₂ [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2715 - 2721

66
[ 40807-61-2 ]
[ 546-43-0 ]
C₂₆H₃₅NO₃ [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2715 - 2721

67
[ 5382-16-1 ]
[ 546-43-0 ]
C₂₀H₃₁NO₃ [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 2715 - 2721

68
[ 120-43-4 ]
[ 546-43-0 ]
(3R,3aR,5S,8aR,9aR)-5,8a-dimethyl-3-[4-(ethoxycarbonyl)piperazin-1-yl]methyl}-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	In methanol; at 20℃; for 12h;	General procedure: Lactone (1 mmol) in MeOH (5 mL) wasstirred, treated with a solution of piperazine (1 mmol) in MeOH (2 mL), and left at room temperature. The course of thereaction was monitored by TLC. If the product did not precipitate, the solvent was evaporated in vacuo after the reaction wascomplete. The residue was recrystallized from a suitable solvent (usually C6H6-hexane mixtures). Compounds 5a-e, 6a-d,and 7a,d,e were prepared by this method.

Reference： [1]Chemistry of Natural Compounds,2019,vol. 55,p. 41 - 46
Khim. Prir. Soedin.,2019,vol. 1,p. 36 - 41,6

69
[ 546-43-0 ]
[ 40172-95-0 ]
(3R,3aR,5S,8aR,9aR)-5,8a-dimethyl-3-[4-(2-furylcarbonyl)piperazin-1-yl]methyl}-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In methanol; at 20℃; for 24h;	General procedure: Lactone (1 mmol) in MeOH (5 mL) wasstirred, treated with a solution of piperazine (1 mmol) in MeOH (2 mL), and left at room temperature. The course of thereaction was monitored by TLC. If the product did not precipitate, the solvent was evaporated in vacuo after the reaction wascomplete. The residue was recrystallized from a suitable solvent (usually C6H6-hexane mixtures). Compounds 5a-e, 6a-d,and 7a,d,e were prepared by this method.

Reference： [1]Chemistry of Natural Compounds,2019,vol. 55,p. 41 - 46
Khim. Prir. Soedin.,2019,vol. 1,p. 36 - 41,6

70
[ 546-43-0 ]
[ 2252-63-3 ]
(3R,3aR,5S,8aR,9aR)-5,8a-dimethyl-3-[4-(4-fluorophenyl)piperazin-1-yl]methyl}-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In methanol; at 20℃; for 6h;	General procedure: Lactone (1 mmol) in MeOH (5 mL) wasstirred, treated with a solution of piperazine (1 mmol) in MeOH (2 mL), and left at room temperature. The course of thereaction was monitored by TLC. If the product did not precipitate, the solvent was evaporated in vacuo after the reaction wascomplete. The residue was recrystallized from a suitable solvent (usually C6H6-hexane mixtures). Compounds 5a-e, 6a-d,and 7a,d,e were prepared by this method.

Reference： [1]Chemistry of Natural Compounds,2019,vol. 55,p. 41 - 46
Khim. Prir. Soedin.,2019,vol. 1,p. 36 - 41,6

71
[ 34803-66-2 ]
[ 546-43-0 ]
(3R,3aR,5S,8aR,9aR)-5,8a-dimethyl-3-[4-(2-pyridyl)piperazin-1-yl]methyl}-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In methanol; at 20℃; for 12h;	General procedure: Lactone (1 mmol) in MeOH (5 mL) wasstirred, treated with a solution of piperazine (1 mmol) in MeOH (2 mL), and left at room temperature. The course of thereaction was monitored by TLC. If the product did not precipitate, the solvent was evaporated in vacuo after the reaction wascomplete. The residue was recrystallized from a suitable solvent (usually C6H6-hexane mixtures). Compounds 5a-e, 6a-d,and 7a,d,e were prepared by this method.

Reference： [1]Chemistry of Natural Compounds,2019,vol. 55,p. 41 - 46
Khim. Prir. Soedin.,2019,vol. 1,p. 36 - 41,6

72
[ 546-43-0 ]
[ 2396-68-1 ]
3-(((4-(tert-butyl)phenyl)thio)methyl)-5,8a-dimethyl-3a,5,6,7,8,8a,9,9a-octahydronaphtho [2,3-b]furan-2(3H)-one [ No CAS ]