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J Agric Food Chem

Title:		"Facile and efficient syntheses of (3Z,6Z,9Z)-3,6,9-nonadecatriene and homologues: pheromone and attractant components of lepidoptera"
Author(s):		Wang S; Zhang A;
Address:		"Department of Entomology, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, USA"
Journal Title:		J Agric Food Chem
Year:		2007
Volume:		20070728
Issue:		17
Page Number:		6929 - 6932
DOI:		10.1021/jf070821o
ISSN/ISBN:		0021-8561 (Print) 0021-8561 (Linking)
Abstract:		"Facile and efficient chemical syntheses of (3Z,6Z,9Z)-3,6,9-nonadecatriene and homologues from commercially available alpha-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 appropriate Grignard reagents proceed very rapidly under notable mild conditions using Li(2)CuCl(4) as catalyst in diethyl ether, and the resulting (3Z,6Z,9Z)-3,6,9-trienes with retention of geometrical configuration were in >92% isolated yield"
Keywords:		Animals Lepidoptera/*chemistry Pheromones/*chemistry Polyenes/*chemical synthesis alpha-Linolenic Acid/chemistry;
Notes:		"MedlineWang, Shifa Zhang, Aijun eng 2007/07/31 J Agric Food Chem. 2007 Aug 22; 55(17):6929-32. doi: 10.1021/jf070821o. Epub 2007 Jul 28"