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,3,4,4aβ,5,6,7,8,8aβ‐Decahydro‐5,5,8aβ‐trimethyl‐2β‐naphthalenyl Acetate, Four Woody Odorants

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.