Facile and efficient syntheses of (3Z,6Z,9Z)-3,6,9-nonadecatriene and homologues: pheromone and attractant components of lepidoptera.
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.
Department of Entomology, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, USA.
Shifa
S
Wang
Aijun
A
Zhang
D000818:Animals; D007915:Lepidoptera / Q000737:chemistry*; D010675:Pheromones / Q000737:chemistry*; D011090:Polyenes / Q000138:chemical synthesis*; D017962:alpha-Linolenic Acid / Q000737:chemistry
C524319:(3Z,6Z,9Z)-3,6,9-nonadecatriene; D010675:Pheromones; D011090:Polyenes; C010411:insect attractants; D017962:alpha-Linolenic Acid