Tetrahedron

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

JN Chakor, L Merlini, S Dallavalle

Index: Chakor, Jyotsna N.; Merlini, Lucio; Dallavalle, Sabrina Tetrahedron, 2011 , vol. 67, # 34 p. 6300 - 6307

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Citation Number: 10

Abstract

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 ...

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