Enantiomerically Pure 4-Methyl- and 1,4-Dimethyl-bicyclo[3.2.0]hept-3-en-6-ols and Ones by Microbial Redox

The reduction of bicyclo[3.2.0]hept-3-en-6-ones 1a,b with Baker’s yeast to a mixture of enantiomerically pure (6S)-endo- and (6S)-exo-alcohols 2a,b and 3a,b respectively is described. Furthermore the oxidation of the racemic endo-alcohols 2a,b with Bacillus stearothermophilus afforded the correspond...

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Published in:Chemistry letters 1996-07, Vol.25 (7), p.511-512
Main Authors: Fantin, Giancarlo, Fogagnolo, Marco, Marotta, Emanuela, Medici, Alessandro, Pedrini, Paola, Righi, Paolo
Format: Article
Language:English
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Summary:The reduction of bicyclo[3.2.0]hept-3-en-6-ones 1a,b with Baker’s yeast to a mixture of enantiomerically pure (6S)-endo- and (6S)-exo-alcohols 2a,b and 3a,b respectively is described. Furthermore the oxidation of the racemic endo-alcohols 2a,b with Bacillus stearothermophilus afforded the corresponding ketones with high enantiomeric excesses resolving the endo-enantiomer. In the same conditions the exo-alcohols 3a,b are not oxidized.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.1996.511