Premium
Enzyme‐Mediated Preparation of the Enantiomerically Enriched Isomers of the Odorous Tetrahydropyranyl Acetates Jasmal ® and Jessemal ® , and Their Olfactory Evaluation
Author(s) -
Abate Agnese,
Brenna Elisabetta,
Fronza Giovanni,
Fuganti Claudio,
Gatti Francesco G.,
Maroncelli Sandro
Publication year - 2006
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200690070
Subject(s) - chemistry , diastereomer , enantiomer , tartaric acid , enzyme , stereochemistry , alcohol , pyran , organic chemistry , resolution (logic) , artificial intelligence , computer science , citric acid
All four stereoisomers of the fragrance Jasmal ® of structure 3,4,5,6‐tetrahydro‐3‐pentyl‐2 H‐ pyran‐4‐yl acetate were prepared by enzymatic resolutions of the corresponding alcohols. The absolute configurations were unambiguously determined by comparison with the enantiomer (3 R ,4 S )‐ 1 prepared from L ‐tartaric acid. The four stereoisomers of the fragrance Jessemal ® of structure 3‐butyl‐5‐methyl‐3,4,5,6‐tetrahydro‐2 H‐ 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 (3 RS ,4 RS ,5 RS )‐ 2 and (3 RS ,4 SR ,5 RS )‐ 2 is also reported.