59633-90-8Relevant articles and documents
191. Preparation and Odor Evaluation of Both Enantiomers of 3,4,4aα,5,6,7,8,8aβ-Octahydro-5,5,8aβ-trimethyl-2(1H)-naphthalenone and 1,2α,3,4,4aα5,6,7,8,8aβ-Decahydro-5,5,8aβ-trimethyl-2β-naphthalenyl Acetate, Four Woody Odorants
Gautier, Antoine,Vial, Christian,Morel, Cedric,Lander, Marina,Naef, Ferdinand
, p. 2039 - 2044 (1987)
The enantiomeric decahydro-2-naphthalenols (+)-5 and (-)-5 were prepared by enantioselective hydrolysis of the racemic chloroacetate (+/-)-2-catalyzed by porcine pancreatic lipase, and converted to the corresponding acetates (+)-1 and (-)-1 and ketones (+)-6 and (-)-6.The absolute configurations of the ketones, alcohols, and acetates were established by chemical correlation with natural manool ((+)-7) by making use of a retro-ene cleavage reaction of the known manool degradation product 8 to (-)-6.A distinct odour difference between the two enantiomers of each pair (+)-1/(-)-1 and (+)-6/(-)-6 has been found.