530099-16-2Relevant articles and documents
Synthesis of hydroxy-substituted unsaturated fatty acids and the amino-acid insect-derivative volicitin
Wei, Han-Xun,Truitt, Christopher L.,Paré, Paul W.
, p. 831 - 833 (2003)
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.