e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Total synthesis of the Fusarium toxin equisetin: Proof of the stereochemical relationship of the tetramate and terpenoid sectors

E Turos, JE Audia, SJ Danishefsky

Index: Turos; Audia; Danishefsky Journal of the American Chemical Society, 1989 , vol. 111, # 21 p. 8231 - 8236

Full Text: HTML

Citation Number: 62

Abstract

Abstract: A total synthesis of the Fusarium mycotoxin equisetin, in a manner that establishes its stereochemistry, is described. The key steps involve a lactonic variation of the ester enolate Claisen rearrangement and a novel construction of a 1-acyltetramic acid from an LN- methylserine derivative and a,% keto ester.

(2R,4aR,5S,6R,8aS)-5-(hydroxymethyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

~%

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde Structure

(1S,2R,4aS,6R,8...

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid Structure

(1S,2R,4aS,6R,8...

~%

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde Structure

(1S,2R,4aS,6R,8...

((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methanol Structure

((1S,2R,4aS,6R,...

~%

methylN-(3-((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-oxopropanoyl)-N-methyl-L-serinate Structure

methylN-(3-((1S...

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde Structure

(1S,2R,4aS,6R,8...

~%

methylN-(3-((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-oxopropanoyl)-N-methyl-L-serinate Structure

methylN-(3-((1S...

(2R,4aR,5S,6R,8aS)-5-(hydroxymethyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

~%

methylN-(3-((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-oxopropanoyl)-N-methyl-L-serinate Structure

methylN-(3-((1S...

(1S,4aR,7R,8aR)-4,7-dimethyl-1-((1E,3E)-penta-1,3-dien-1-yl)tetrahydro-1H-isochromene-3,8(4H,8aH)-dione Structure

(1S,4aR,7R,8aR)...

~%

methylN-(3-((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-oxopropanoyl)-N-methyl-L-serinate Structure

methylN-(3-((1S...

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid Structure

(1S,2R,4aS,6R,8...

~%

methylN-(3-((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-oxopropanoyl)-N-methyl-L-serinate Structure

methylN-(3-((1S...

(1S,4aR,7R,8aR)-4,7-dimethyl-1-((1E,3E)-penta-1,3-dien-1-yl)tetrahydro-1H-isochromene-3,8(4H,8aH)-dione Structure

(1S,4aR,7R,8aR)...

~%

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde Structure

(1S,2R,4aS,6R,8...

(1S,2R,4aS,6R,8aR)-methyl 1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate Structure

(1S,2R,4aS,6R,8...

~%

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde Structure

(1S,2R,4aS,6R,8...

tert-butyl(((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methoxy)dimethylsilane Structure

tert-butyl(((1S...

~%

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde Structure

(1S,2R,4aS,6R,8...

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

~%

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbaldehyde Structure

(1S,2R,4aS,6R,8...

(1S,4aR,7R,8aR)-4,7-dimethyl-1-((1E,3E)-penta-1,3-dien-1-yl)tetrahydro-1H-isochromene-3,8(4H,8aH)-dione Structure

(1S,4aR,7R,8aR)...

~%

(1S,2R,4aS,8aR)-trimethylsilyl 1,6-dimethyl-2-((E)-prop-1-en-1-yl)-5-((trimethylsilyl)oxy)-1,2,4a,7,8,8a-hexahydronaphthalene-1-carboxylate Structure

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

(((1S,4aR,8aR)-4,7-dimethyl-1-((1E,3E)-penta-1,3-dien-1-yl)-4a,5,6,8a-tetrahydro-1H-isochromene-3,8-diyl)bis(oxy))bis(trimethylsilane) Structure

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

~%

(1S,2R,4aS,8aR)-trimethylsilyl 1,6-dimethyl-2-((E)-prop-1-en-1-yl)-5-((trimethylsilyl)oxy)-1,2,4a,7,8,8a-hexahydronaphthalene-1-carboxylate Structure

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

tert-butyl(((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methoxy)dimethylsilane Structure

tert-butyl(((1S...

~97%

((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methanol Structure

((1S,2R,4aS,6R,...

(2R,4aR,5S,6R,8aS)-5-(hydroxymethyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

~%

((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methanol Structure

((1S,2R,4aS,6R,...

(1S,4aR,7R,8aR)-4,7-dimethyl-1-((1E,3E)-penta-1,3-dien-1-yl)tetrahydro-1H-isochromene-3,8(4H,8aH)-dione Structure

(1S,4aR,7R,8aR)...

~%

((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methanol Structure

((1S,2R,4aS,6R,...

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid Structure

(1S,2R,4aS,6R,8...

~%

((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methanol Structure

((1S,2R,4aS,6R,...

(1S,2R,4aS,6R,8aR)-methyl 1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate Structure

(1S,2R,4aS,6R,8...

~%

((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methanol Structure

((1S,2R,4aS,6R,...

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl methanesulfonate Structure

(2R,4aR,5S,6R,8...

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

~90%

tert-butyl(((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methoxy)dimethylsilane Structure

tert-butyl(((1S...

(2R,4aR,5S,6R,8aS)-5-(hydroxymethyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

~%

tert-butyl(((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methoxy)dimethylsilane Structure

tert-butyl(((1S...

(1S,4aR,7R,8aR)-4,7-dimethyl-1-((1E,3E)-penta-1,3-dien-1-yl)tetrahydro-1H-isochromene-3,8(4H,8aH)-dione Structure

(1S,4aR,7R,8aR)...

~%

tert-butyl(((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methoxy)dimethylsilane Structure

tert-butyl(((1S...

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid Structure

(1S,2R,4aS,6R,8...

~%

tert-butyl(((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methoxy)dimethylsilane Structure

tert-butyl(((1S...

(1S,2R,4aS,6R,8aR)-methyl 1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate Structure

(1S,2R,4aS,6R,8...

~%

tert-butyl(((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methoxy)dimethylsilane Structure

tert-butyl(((1S...

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

~%

tert-butyl(((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methoxy)dimethylsilane Structure

tert-butyl(((1S...

Methanesulfonyl chloride Structure

Methanesulfonyl...

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

~92%

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl methanesulfonate Structure

(2R,4aR,5S,6R,8...

(2R,4aR,5S,6R,8aS)-5-(hydroxymethyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

~%

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl methanesulfonate Structure

(2R,4aR,5S,6R,8...

(1S,4aR,7R,8aR)-4,7-dimethyl-1-((1E,3E)-penta-1,3-dien-1-yl)tetrahydro-1H-isochromene-3,8(4H,8aH)-dione Structure

(1S,4aR,7R,8aR)...

~%

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl methanesulfonate Structure

(2R,4aR,5S,6R,8...

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid Structure

(1S,2R,4aS,6R,8...

~%

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl methanesulfonate Structure

(2R,4aR,5S,6R,8...

(1S,2R,4aS,6R,8aR)-methyl 1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate Structure

(1S,2R,4aS,6R,8...

~%

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl methanesulfonate Structure

(2R,4aR,5S,6R,8...

(1S,2R,4aS,8aR)-trimethylsilyl 1,6-dimethyl-2-((E)-prop-1-en-1-yl)-5-((trimethylsilyl)oxy)-1,2,4a,7,8,8a-hexahydronaphthalene-1-carboxylate Structure

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

~%

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl methanesulfonate Structure

(2R,4aR,5S,6R,8...

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl methanesulfonate Structure

(2R,4aR,5S,6R,8...

tert-butyl(((1S,2R,4aS,6R,8aR)-1,6-dimethyl-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)methoxy)dimethylsilane Structure

tert-butyl(((1S...

~92%

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

(1S,4aR,7R,8aR)-4,7-dimethyl-1-((1E,3E)-penta-1,3-dien-1-yl)tetrahydro-1H-isochromene-3,8(4H,8aH)-dione Structure

(1S,4aR,7R,8aR)...

~%

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid Structure

(1S,2R,4aS,6R,8...

~%

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

(1S,2R,4aS,6R,8aR)-methyl 1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate Structure

(1S,2R,4aS,6R,8...

~%

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

(1S,2R,4aS,8aR)-trimethylsilyl 1,6-dimethyl-2-((E)-prop-1-en-1-yl)-5-((trimethylsilyl)oxy)-1,2,4a,7,8,8a-hexahydronaphthalene-1-carboxylate Structure

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

~%

(2R,4aR,5S,6R,8aS)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

(1S,2R,4aS,6R,8aR)-methyl 1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate Structure

(1S,2R,4aS,6R,8...

~%

(2R,4aR,5S,6R,8aS)-5-(hydroxymethyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

(1S,4aR,7R,8aR)-4,7-dimethyl-1-((1E,3E)-penta-1,3-dien-1-yl)tetrahydro-1H-isochromene-3,8(4H,8aH)-dione Structure

(1S,4aR,7R,8aR)...

~%

(2R,4aR,5S,6R,8aS)-5-(hydroxymethyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid Structure

(1S,2R,4aS,6R,8...

~%

(2R,4aR,5S,6R,8aS)-5-(hydroxymethyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

(1S,2R,4aS,8aR)-trimethylsilyl 1,6-dimethyl-2-((E)-prop-1-en-1-yl)-5-((trimethylsilyl)oxy)-1,2,4a,7,8,8a-hexahydronaphthalene-1-carboxylate Structure

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

~%

(2R,4aR,5S,6R,8aS)-5-(hydroxymethyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

(((1S,4aR,8aR)-4,7-dimethyl-1-((1E,3E)-penta-1,3-dien-1-yl)-4a,5,6,8a-tetrahydro-1H-isochromene-3,8-diyl)bis(oxy))bis(trimethylsilane) Structure

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

~%

(2R,4aR,5S,6R,8aS)-5-(hydroxymethyl)-2,5-dimethyl-6-((E)-prop-1-en-1-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol Structure

(2R,4aR,5S,6R,8...

(1S,4aR,7R,8aR)-4,7-dimethyl-1-((1E,3E)-penta-1,3-dien-1-yl)tetrahydro-1H-isochromene-3,8(4H,8aH)-dione Structure

(1S,4aR,7R,8aR)...

~%

(1S,2R,4aS,6R,8aR)-methyl 1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate Structure

(1S,2R,4aS,6R,8...

(1S,2R,4aS,8aR)-trimethylsilyl 1,6-dimethyl-2-((E)-prop-1-en-1-yl)-5-((trimethylsilyl)oxy)-1,2,4a,7,8,8a-hexahydronaphthalene-1-carboxylate Structure

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

~%

(1S,2R,4aS,6R,8aR)-methyl 1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate Structure

(1S,2R,4aS,6R,8...

(((1S,4aR,8aR)-4,7-dimethyl-1-((1E,3E)-penta-1,3-dien-1-yl)-4a,5,6,8a-tetrahydro-1H-isochromene-3,8-diyl)bis(oxy))bis(trimethylsilane) Structure

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

~%

(1S,2R,4aS,6R,8aR)-methyl 1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate Structure

(1S,2R,4aS,6R,8...

(1S,2R,4aS,8aR)-trimethylsilyl 1,6-dimethyl-2-((E)-prop-1-en-1-yl)-5-((trimethylsilyl)oxy)-1,2,4a,7,8,8a-hexahydronaphthalene-1-carboxylate Structure

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

~%

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid Structure

(1S,2R,4aS,6R,8...

(1S,4aR,7R,8aR)-4,7-dimethyl-1-((1E,3E)-penta-1,3-dien-1-yl)tetrahydro-1H-isochromene-3,8(4H,8aH)-dione Structure

(1S,4aR,7R,8aR)...

~%

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid Structure

(1S,2R,4aS,6R,8...

(((1S,4aR,8aR)-4,7-dimethyl-1-((1E,3E)-penta-1,3-dien-1-yl)-4a,5,6,8a-tetrahydro-1H-isochromene-3,8-diyl)bis(oxy))bis(trimethylsilane) Structure

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

~%

(1S,2R,4aS,6R,8aR)-1,6-dimethyl-5-oxo-2-((E)-prop-1-en-1-yl)-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid Structure

(1S,2R,4aS,6R,8...