Enzyme-mediated preparation of the enantiomerically enriched isomers of the odorous tetrahydropyranyl acetates Jasmal and Jessemal, and their olfactory evaluation.

All four stereoisomers of the fragrance Jasmal of structure 3,4,5,6-tetrahydro-3-pentyl-2H-pyran-4-yl acetate were prepared by enzymatic resolutions of the corresponding alcohols. The absolute configurations were unambiguously determined by comparison with the enantiomer (3R,4S)-1 prepared from L-tartaric acid. The four stereoisomers of the fragrance Jessemal of structure 3-butyl-5-methyl-3,4,5,6-tetrahydro-2H-pyran-4-yl acetate were obtained starting from the epoxy alcohol 10, which was obtained in an optically pure state by enzymatic resolution of the racemic mixture.