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Issue 22, 2000
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Baker’s yeast-mediated enantioselective synthesis of the bisabolane sesquiterpenes (+)-curcuphenol, (+)-xanthorrhizol, (−)-curcuquinone and (+)-curcuhydroquinone

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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.

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Publication details

The article was received on 28 Jul 2000, accepted on 11 Sep 2000 and first published on 30 Oct 2000


Article type: Paper
DOI: 10.1039/B006141G
Citation: J. Chem. Soc., Perkin Trans. 1, 2000, 3758-3764
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    Baker’s yeast-mediated enantioselective synthesis of the bisabolane sesquiterpenes (+)-curcuphenol, (+)-xanthorrhizol, (−)-curcuquinone and (+)-curcuhydroquinone

    C. Fuganti and S. Serra, J. Chem. Soc., Perkin Trans. 1, 2000, 3758
    DOI: 10.1039/B006141G

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