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Selective synthesis of 1-, and 3-carbomethoxy 2-tetralol stereoisomers by microbial reduction of the corresponding tetralones

✍ Scribed by Cécile Abalain; Didier Buisson; Robert Azerad

Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
803 KB
Volume
7
Category
Article
ISSN
0957-4166

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✦ Synopsis

The microbial reduction of ~-ketoesters derived from 2-tetralone has been shown to produce good yields of 2-hydroxy-l-carboxy-or 3-hydroxy-2-carboxyesters. Baker's yeast invariably affords a high enantiomeric purity cis-hydroxyester, while fungi strains may produce, sometimes exclusively, cisor transcomplementary stereochemistries. From a general survey of the baker's yeast reduction of cyclic 13-ketoesters, a working model for predicting enantio-and diastereoselectivities of the reduction is proposed and discussed.

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