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Tetrahedron letters

Synthesis of (-)-ambrox from ℓ-abietic acid

H Koyama, Y Kaku, M Ohno

文献索引：Koyama, Hiroo; Kaku, Yumiko; Ohno, Masaji Tetrahedron Letters, 1987 ,  vol. 28,  # 25  p. 2863 - 2866

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被引用次数: 39

摘要

Synthesis of (-)-ambrox 1 has been completed stereoselectively starting from P,-abietic acid 2. is a constituent of ambergris; naturally occurring fragrance Ambergris is obtained as internal concretion of sperm whale, and has been highly valued in perfumery industry because of its strong and tenacious odour. However, owing to the diminishing availability of the whale, a number of synthetic approaches have been studied toward ambrox 1) and ...

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2-((1S,4aR,8aR)-5-(hydroxymethyl)-2,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)ethanol结构式

113308-64-8

2-((1S,4aR,8aR)...

~%

(1R,2R,4aR,8aS)-1-(2-hydroxyethyl)-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-2-ol结构式

113308-70-6

(1R,2R,4aR,8aS)...

(4aR,5S,8aR)-methyl 1,4a,6-trimethyl-5-(2-oxoethyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate结构式

113308-63-7

(4aR,5S,8aR)-me...

~%

(1R,2R,4aR,8aS)-1-(2-hydroxyethyl)-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-2-ol结构式

113308-70-6

(1R,2R,4aR,8aS)...

(4aR,5S,8aR)-methyl 1,4a,6-trimethyl-5-(4-methyl-3-oxopentyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate结构式

113308-61-5

(4aR,5S,8aR)-me...

~%

(1R,2R,4aR,8aS)-1-(2-hydroxyethyl)-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-2-ol结构式

113308-70-6

(1R,2R,4aR,8aS)...

(4aR,5S,8aR)-methyl 1,4a,6-trimethyl-5-((E)-4-methyl-3-((trimethylsilyl)oxy)pent-2-en-1-yl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate结构式

113308-62-6

(4aR,5S,8aR)-me...

~%

(1R,2R,4aR,8aS)-1-(2-hydroxyethyl)-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-2-ol结构式

113308-70-6

(1R,2R,4aR,8aS)...

(4aR,5S,8aR)-methyl 1,4a,6-trimethyl-5-(2-oxoethyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate结构式

113308-63-7

(4aR,5S,8aR)-me...

~85%

2-((1S,4aR,8aR)-5-(hydroxymethyl)-2,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)ethanol结构式

113308-64-8

2-((1S,4aR,8aR)...

(4aR,5S,8aR)-methyl 1,4a,6-trimethyl-5-((E)-4-methyl-3-((trimethylsilyl)oxy)pent-2-en-1-yl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate结构式

113308-62-6

(4aR,5S,8aR)-me...

~51%

(4aR,5S,8aR)-methyl 1,4a,6-trimethyl-5-(2-oxoethyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate结构式

113308-63-7

(4aR,5S,8aR)-me...

(4aR,5S,8aR)-methyl 1,4a,6-trimethyl-5-(4-methyl-3-oxopentyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate结构式

113308-61-5

(4aR,5S,8aR)-me...

~%

(4aR,5S,8aR)-methyl 1,4a,6-trimethyl-5-(2-oxoethyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate结构式

113308-63-7

(4aR,5S,8aR)-me...

(1R,2R,4aR,8aS)-1-(2-hydroxyethyl)-5-(hydroxymethyl)-2,5,8a-trimethyldecahydronaphthalen-2-ol结构式

113308-70-6

(1R,2R,4aR,8aS)...

~%

结构式

113327-33-6

2-((1S,4aR,8aR)-5-(hydroxymethyl)-2,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)ethanol结构式

113308-64-8

2-((1S,4aR,8aR)...

~%

结构式

113327-33-6

(4aR,5S,8aR)-methyl 1,4a,6-trimethyl-5-(2-oxoethyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate结构式

113308-63-7

(4aR,5S,8aR)-me...

~%

结构式

113327-33-6

(4aR,5S,8aR)-methyl 1,4a,6-trimethyl-5-(4-methyl-3-oxopentyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate结构式

113308-61-5

(4aR,5S,8aR)-me...

~%

结构式

113327-33-6

(1R,2R,4aR,8aS)-1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5,8a-trimethyldecahydronaphthalen-2-ol结构式

113308-69-3

(1R,2R,4aR,8aS)...

~%

结构式

113327-33-6

tert-butyl(((1R,2R,4aR,8aS)-1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-5,8a-dimethyloctahydro-1H-spiro[naphthalene-2,2'-oxiran]-5-yl)methoxy)dimethylsilane结构式

113308-68-2

tert-butyl(((1R...

~%

结构式

113327-33-6

2-((1S,4aR,8aR)-5-(hydroxymethyl)-2,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)ethanol结构式

113308-64-8

2-((1S,4aR,8aR)...

~%

tert-butyl(((1R,2R,4aR,8aS)-1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-5,8a-dimethyloctahydro-1H-spiro[naphthalene-2,2'-oxiran]-5-yl)methoxy)dimethylsilane结构式

113308-68-2

tert-butyl(((1R...

(4aR,5S,8aR)-methyl 1,4a,6-trimethyl-5-(2-oxoethyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate结构式

113308-63-7

(4aR,5S,8aR)-me...

~%

tert-butyl(((1R,2R,4aR,8aS)-1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-5,8a-dimethyloctahydro-1H-spiro[naphthalene-2,2'-oxiran]-5-yl)methoxy)dimethylsilane结构式

113308-68-2

tert-butyl(((1R...

(4aR,5S,8aR)-methyl 1,4a,6-trimethyl-5-(4-methyl-3-oxopentyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate结构式

113308-61-5

(4aR,5S,8aR)-me...

~%

tert-butyl(((1R,2R,4aR,8aS)-1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-5,8a-dimethyloctahydro-1H-spiro[naphthalene-2,2'-oxiran]-5-yl)methoxy)dimethylsilane结构式

113308-68-2

tert-butyl(((1R...

(4aR,5S,8aR)-methyl 1,4a,6-trimethyl-5-(4-methyl-3-oxopentyl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate结构式

113308-61-5

(4aR,5S,8aR)-me...

~%

2-((1S,4aR,8aR)-5-(hydroxymethyl)-2,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)ethanol结构式

113308-64-8

2-((1S,4aR,8aR)...

(4aR,5S,8aR)-methyl 1,4a,6-trimethyl-5-((E)-4-methyl-3-((trimethylsilyl)oxy)pent-2-en-1-yl)-1,2,3,4,4a,5,8,8a-octahydronaphthalene-1-carboxylate结构式

113308-62-6

(4aR,5S,8aR)-me...

~%

2-((1S,4aR,8aR)-5-(hydroxymethyl)-2,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)ethanol结构式

113308-64-8

2-((1S,4aR,8aR)...


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