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

Agnese Abate, Elisabetta Brenna, Giovanni Fronza, Claudio Fuganti, Francesco G Gatti, Sandro Maroncelli

Dipartimento di Chimica, Materiali ed Ingegneria Chimica, Politecnico di Milano, Via Mancinelli 7, I-20131 Milano, Italy.

Chemistry & biodiversity 2006 Jun

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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. The olfactory evaluations of all stereoisomers are reported. (1)H-NMR Conformational analysis of diastereoisomers (3RS,4RS,5RS)-2 and (3RS,4SR,5RS)-2 is also reported.

Citation

Agnese Abate, Elisabetta Brenna, Giovanni Fronza, Claudio Fuganti, Francesco G Gatti, Sandro Maroncelli. Enzyme-mediated preparation of the enantiomerically enriched isomers of the odorous tetrahydropyranyl acetates Jasmal and Jessemal, and their olfactory evaluation. Chemistry & biodiversity. 2006 Jun;3(6):677-94