Enzyme-mediated preparation of the single enantiomers of the olfactory active components of the woody odorant Timberol (R)

Citation
E. Brenna et al., Enzyme-mediated preparation of the single enantiomers of the olfactory active components of the woody odorant Timberol (R), HELV CHIM A, 82(10), 1999, pp. 1762-1773
Citations number
14
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
HELVETICA CHIMICA ACTA
ISSN journal
0018019X → ACNP
Volume
82
Issue
10
Year of publication
1999
Pages
1762 - 1773
Database
ISI
SICI code
0018-019X(1999)82:10<1762:EPOTSE>2.0.ZU;2-U
Abstract
Enantiomerically pure (3S)-3a and -3b, the olfactory active forms of 1-(2,2 ,6-trimethylcyclohexyl)hexan-3-ol. components of the commercial woody odora nt Timberol(R), are obtained by lipase-PS-mediated enantioselective acetyla tion of the allylic alcohols 6 and 7 and of the saturated alcohol 3. These materials, as mixtures of diastereoisomers, provided (3R)-configured transf ormation products. However, whereas in the conversion of 6 and 7 there is n o diastereoselection, 3 provided the acetate of (1'S,3R,6'R)-3c much more r apidly than that of the diastereoisomer (1'R,3R,6'S)-3d (Scheme 3). Inversi on of the configuration at C(3) of the side chain of the olfactory inactive (3R)-materials obtained as acetates in the enzymic treatment of 6, 7, and 3 also provided, eventually, the desired olfactory active (3S)-products.