4.4 Article

Enantioselective total synthesis and absolute configuration of the alleged structure of crassinervic acid

期刊

TETRAHEDRON
卷 67, 期 34, 页码 6300-6307

出版社

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.06.015

关键词

Antifungal; Natural products; Enantioselective; Synthesis

资金

  1. University of Milan

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An enantioselective synthesis of the structure reported for the natural antifungal compound, (-)-crassinervic acid (1), has been achieved starting from geraniol and p-hydroxybenzoic acid. The key chirality-inducing step is a Sharpless asymmetric epoxidation of an allylic alcohol, on the basis of which the S configuration can be assigned to the (-) natural enantiomer. The discrepancies between the spectroscopic data for synthetic and natural crassinervic acid cast some doubts on the structure assigned to the natural compound. A possible revised structure is discussed. (C) 2011 Elsevier Ltd. All rights reserved.

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