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Issue 6, 1979
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Biosynthesis of echinulin. The stereochemistry of aromatic isoprenylation

Abstract

The incorporation of [1,2-13C]acetate into echinulin has shown that the aromatic isoprenylation at the 5- and 7-positions occurs without any change in stereochemistry around the double bond of the dimethyl-allyl group and chemical degradation of echinulin, obtained by feeding [5(R)-3H]- and [5(S)-3H]mevalonate, to isopentylamine and oxidation with pea seedling diamine oxidase has shown that the isoprenylation reactions at positions 5- and 7- proceed with inversion of configuration at the allylic pyrophosphate.

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Article information


J. Chem. Soc., Chem. Commun., 1979, 280-282
Article type
Paper

Biosynthesis of echinulin. The stereochemistry of aromatic isoprenylation

J. K. Allen, K. D. Barrow and A. J. Jones, J. Chem. Soc., Chem. Commun., 1979, 280 DOI: 10.1039/C39790000280

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