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Enzyme‐Mediated Preparation of the Single Enantiomers of the Olfactory Active Components of the Woody Odorant Timberol ®
Author(s) -
Brenna Elisabetta,
Fronza Giovanni,
Fuganti Claudio,
Righetti Annalisa,
Serra Stefano
Publication year - 1999
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(19991006)82:10<1762::aid-hlca1762>3.0.co;2-1
Subject(s) - chemistry , diastereomer , enantiomer , enzyme , acetylation , enantioselective synthesis , stereochemistry , absolute configuration , lipase , organic chemistry , biochemistry , catalysis , gene
Enantiomerically pure (3 S )‐ 3a and ‐ 3b , the olfactory active forms of 1‐(2,2,6‐trimethylcyclohexyl)hexan‐ 3‐ol, components of the commercial woody odorant Timberol ® , are obtained by lipase‐PS‐mediated enantioselective acetylation of the allylic alcohols 6 and 7 and of the saturated alcohol 3 . These materials, as mixtures of diastereoisomers, provided (3 R )‐configured transformation products. However, whereas in the conversion of 6 and 7 there is no diastereoselection, 3 provided the acetate of (1′ S ,3 R ,6′ R )‐ 3c much more rapidly than that of the diastereoisomer (1′ R ,3 R ,6′ S )‐ 3d ( Scheme 3 ). Inversion of the configuration at C(3) of the side chain of the olfactory inactive (3 R )‐materials obtained as acetates in the enzymic treatment of 6 , 7 , and 3 also provided, eventually, the desired olfactory active (3 S )‐products.