Synthesis of hydroxy-substituted unsaturated fatty acids and the amino-acid insect-derivative volicitin

Han Xun Wei, Christopher L. Truitt, Paul W. Paré

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

An efficient synthesis of N-(17S-hydroxylinolenoyl)-L-glutamine (volicitin), a chemical elicitor from the herbivore-pest beet armyworm is presented. The synthesis, which utilizes a copper-catalyzed acetylene coupling, links (S)-3,6-heptadiyne-2-ol with a C-8 propargylic iodine methyl ester to form the (S)-17-hydroxylinolenate skeleton. By substituting different heptadiyne-2-ol groups, a series of methylene interrupted polyacetylene analogues were generated.

Original languageEnglish
Pages (from-to)831-833
Number of pages3
JournalTetrahedron Letters
Volume44
Issue number4
DOIs
StatePublished - Jan 20 2003

Fingerprint

Dive into the research topics of 'Synthesis of hydroxy-substituted unsaturated fatty acids and the amino-acid insect-derivative volicitin'. Together they form a unique fingerprint.

Cite this