Issue 1, 2000

Baker’s yeast mediated enantioselective synthesis of the bisabolene sesquiterpenes (+)-epijuvabione and (−)-juvabione

Abstract

Fermenting baker’s yeast converts the unsaturated aldehydes 7 and 11 into the saturated alcohols 8 and 12, respectively. The microbial saturation of the double bond proceeds in high chemical yields and the stereoselectivity of the reduction is strongly influenced by the EZ ratio of the substrate. Enantiopure 8 and 12 are chiral building blocks for the synthesis of bisabolene sesquiterpenes and their usefulness is shown in the preparation of (+)-epijuvabione 1 and (−)-juvabione 3.

Article information

Article type
Paper
Submitted
23 Jul 1999
Accepted
25 Oct 1999
First published
24 Dec 1999

J. Chem. Soc., Perkin Trans. 1, 2000, 97-101

Baker’s yeast mediated enantioselective synthesis of the bisabolene sesquiterpenes (+)-epijuvabione and (−)-juvabione

C. Fuganti and S. Serra, J. Chem. Soc., Perkin Trans. 1, 2000, 97 DOI: 10.1039/A905977F

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