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

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

doi:10.1016/S0040-4039(02)02640-0

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 journal › Article › peer-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 language	English
Pages (from-to)	831-833
Number of pages	3
Journal	Tetrahedron Letters
Volume	44
Issue number	4
DOIs	https://doi.org/10.1016/S0040-4039(02)02640-0
State	Published - Jan 20 2003

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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.",

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AU - Wei, Han Xun

AU - Truitt, Christopher L.

AU - Paré, Paul W.

PY - 2003/1/20

Y1 - 2003/1/20

N2 - 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.

AB - 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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DO - 10.1016/S0040-4039(02)02640-0

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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