Chemoenzymatic synthesis of (S)- and (R)-γ-cyclogeraniols

For the purpose of the production of expensive perfume such as ambrein, (S)- and (R)-γ-cyclogeraniols (2) seem to be the important chiral synthons for the synthesis of ambrein The lipase QL from Alcaligenes sp.-catalyzed enantioselective acetylation of the (±)-(1,2)-trans-6,6-dimethyl-2-hydroxyhexane-1-carboxylate (9) was carried out and an alcohol (1S, 2S)-9 and an acetate (1R, 2R)-10 possessing high enantiomeric excess (>99% ee), respectively, were obtained. Both the alcohol (1S, 2S)-9 and the acetate (1R, 2R)-10 were converted to the (S)- and (R)-γ-cyclogeraniols (2), respectively.