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Title: Facile and Efficient Syntheses of (3Z,6Z,9Z)-3,6,9-Nonadecatriene and Homologs: Pheromone and Attractant Components of Lepidoptera

Author
item Wang, Shifa
item Zhang, Aijun

Submitted to: Journal of Agriculture and Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 6/19/2007
Publication Date: 7/28/2007
Citation: Wang, S., Zhang, A. 2007. Facile and Efficient Syntheses of (3Z,6Z,9Z)-3,6,9-Nonadecatriene and Homologs: Pheromone and Attractant Components of Lepidoptera. Journal of Agriculture and Food Chemistry. 55(17):6929-6932.

Interpretive Summary: The numerous moths distributed worldwide utilize certain type of common compounds as the sex attractant for mate location. Because this type of compound can be used in integrated pest management to protect many agricultural important corps, a number of different synthetic methodologies have been developed. However, those methods require long reaction time; involve multiple steps; and give low yields. We developed a new method, which could afford this type of compound in short time and less steps but gave high yield from the commercially available starting material. Therefore, the facile and efficient syntheses of the attractants should make this type of compound easily accessible to the farmers and scientists and facilitate the pest management program to protect many agricultural important corps from moth damage.

Technical Abstract: Facile and efficient chemical syntheses of (3Z,6Z,9Z)-3,6,9-nonadecatriene and homologs from commercially available '-linolenic acid [(9Z,12Z,15Z)-9,12,15-octadecatrienoic acid] are reported. These straight-chain homoconjugated trienes are common sex pheromone and attractant components for many lepidopterous insect pests. The metal catalyzed cross-coupling reactions between (9Z,12Z,15Z)-9,12,15-octadecatrienyl triflate and the appropriated Grignard reagents proceed very rapidly under notable mild conditions using Li2CuCl4 as catalyst in diethyl ether and resulting (3Z,6Z,9Z)-3,6,9-trienes with retention of geometrical configuration were in >92% isolated yield.