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Issue 0, 1985
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Total synthesis of cyclopentanoid natural products

Abstract

The highly functionalised bicyclo[3.3.0]octanes (5) and (6) have been prepared by a sequence involving intramolecular Wittig reactions of the diketo ester (9) with vinyl phosphonium salts (3) and (4). Compounds (5) and (6) have then been used as starting materials for formal syntheses of (±)-chrysomelidial, (±)-loganin, and (±)-hirsutene. An intermediate used in the synthesis of (5) and (6) has been converted into a known precursor of (±)-sarkomycin.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1985, 2625-2635
Article type
Paper

Total synthesis of cyclopentanoid natural products

A. T. Hewson and D. T. MacPherson, J. Chem. Soc., Perkin Trans. 1, 1985, 2625
DOI: 10.1039/P19850002625

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