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

✍ Scribed by Han-Xun Wei; Christopher L. Truitt; Paul W. Paré

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
143 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

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