Microbial reduction of varying size cyclic β-ketoesters. : Stereoselective synthesis of chiral lactones and epoxides

The reduction of four- to eight-membered cyclic β-ketoesters to the corresponding β-hydroxyesters by various yeasts and fungi is described. The microbial reduction of ethyl cyclobutanone 2-carboxylate is reported for the first time. The different stereospecificities observed in these reductions invo...

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Bibliographic Details
Published in:Journal of molecular catalysis. B, Enzymatic Enzymatic, 1998-09, Vol.5 (1), p.255-259
Main Authors: Danchet, Sylvie, Buisson, Didier, Azerad, Robert
Format: Article
Language:English
Subjects:
1-Cyclobutanol-2-carboxylate
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Diastereoselectivity
Dynamic kinetic resolution
Enantiospecificity
Fundamental and applied biological sciences. Psychology
Methods. Procedures. Technologies
β-Hydroxyester
ω-Epoxyester
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Summary:The reduction of four- to eight-membered cyclic β-ketoesters to the corresponding β-hydroxyesters by various yeasts and fungi is described. The microbial reduction of ethyl cyclobutanone 2-carboxylate is reported for the first time. The different stereospecificities observed in these reductions involving a dynamic kinetic resolution are analysed. The enantiopure reduction products have been used in the synthesis of both enantiomers of functionalized lactones and epoxides.
ISSN:1381-1177
1873-3158
DOI:10.1016/S1381-1177(98)00045-9