Baker’s yeast-mediated enantioselective synthesis of the bisabolane sesquiterpenes (+)-curcuphenol, (+)-xanthorrhizol, (−)-curcuquinone and (+)-curcuhydroquinone
- 30 October 2000
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 22,p. 3758-3764
- https://doi.org/10.1039/b006141g
Abstract
Fermenting baker’s yeast converts the unsaturated aldehydes 5a–c into the saturated alcohols 6a–c, respectively. The microbial saturation of substrates adsorbed on a nonpolar resin proceeds in high chemical yields and shows complete enantioselectivity in the formation of the (S)-(+) isomers. Enantiopure 6a–c are versatile chiral building blocks for the synthesis of bisabolane sesquiterpenes. Their usefulness is shown in the preparation of (S)-(+)-curcuphenol, (S)-(+)-xanthorrhizol, (S)-(−)-curcuquinone and (S)-(+)-curcuhydroquinone.Keywords
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