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July 19, 2002The Journal of Organic Chemistry

Synthesis of Mayolene-16 and Mayolene-18: Larval Defensive Lipids from the European Cabbage Butterfly

Douglas B. Weibel Laura E. Shevy Frank C. Schroeder Jerrold Meinwald

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Abstract

A tandem Wittig approach has been employed for the synthesis of both (11S,9Z,12Z,15Z)- and (11R,9Z,12Z,15Z)-hydroxyoctadeca-9,12,15-trienoic acid (11-hydroxylinolenic acid, 11-HLA) from (R)-glyceraldehyde acetonide. From (11R)-HLA we have prepared the corresponding palmitic acid and stearic acid esters, mayolene-16 (1) and mayolene-18 (2), insect defensive compounds recently identified from Pieris rapae larvae. In addition, we describe the synthesis of three macrocyclic oligomers (24-26) derived from (11R)-HLA.

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Weibel et al. (2002) studied this question.

synapsesocial.com/papers/6ac852a2b41b58b9b81febab https://doi.org/10.1021/jo011102q

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