Tetrahedron letters

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

H Koyama, Y Kaku, M Ohno

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

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Citation Number: 39

Abstract

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 ...

 Related Synthetic Route
2-((1S,4aR,8aR)-5-(hydroxymethyl)-2,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)ethanol Structure

113308-64-8

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

~%

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

113308-70-6

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

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113308-63-7

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

~%

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

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 Structure

113308-61-5

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

~%

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

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 Structure

113308-62-6

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

~%

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

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 Structure

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 Structure

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 Structure

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 Structure

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 Structure

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 Structure

113308-63-7

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

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113308-70-6

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

~%

Structure

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 Structure

113308-64-8

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

~%

Structure

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 Structure

113308-63-7

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

~%

Structure

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 Structure

113308-61-5

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

~%

Structure

113327-33-6

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

113308-69-3

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

~%

Structure

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 Structure

113308-68-2

tert-butyl(((1R...

~%

Structure

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 Structure

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 Structure

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 Structure

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 Structure

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 Structure

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 Structure

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 Structure

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 Structure

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 Structure

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 Structure

113308-64-8

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


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