Synthesis of volicitin: a novel three-component Wittig approach to chiral 17-hydroxylinolenic acid

Abstract

A short stereoselective synthesis of both enantiomers of N-(17-hydroxylinolenoyl)-L-glutamine (volicitin) 12, an elicitor of plant volatile biosynthesis from beet armyworm salivary secretion, is described; the protected 17-hydroxylinolenic acid 4 moiety of volicitin 12 was prepared in a one pot bis-Wittig reaction.

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