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Facile and efficient syntheses of (3Z,6Z,9Z)-3,6,9-nonadecatriene and homologues: pheromone and attractant components of lepidoptera.

Wang S, Zhang A

Department of Entomology, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, USA.

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.

Published 16 August 2007 in J Agric Food Chem, 55(17): 6929-32.
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