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

Article abstract of DOI:10.1002/hlca.19870700809

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.