Department of Entomology, University of California, 92521, Riverside, California.
J Chem Ecol. 1991 May;17(5):911-29. doi: 10.1007/BF01395599.
Enantiomerically enriched forms of (Z)-6-cis-9,10-epoxymonoenes and (Z)-9-cis-6,7-epoxymonoenes of chain lengths C17-20 were synthesized by Sharpless asymmetric epoxidation of allylic alcohol intermediates, followed by tosylation or halogenation and chain extension. The resulting monounsaturated epoxides were field tested as sex attractants for lepidopteran species.Euchlaena madusaria Walker males were attracted to blends of the enantiomers of (Z)-6- cis- 9,10-epoxynonadecene 6Z-cis-9,10-epoxy-19:H; IUPAC name [2α,3α(Z)]-2-pentyl-3-(2-dodecenyI)oxirane in combination with 6Z,9Z-19: H. The response was antagonized by 9Z-cis-6,7-epoxy-19: H. 6Z,9Z-19: H was tentatively identified in pheromone gland extracts.Xanthotype sospeta Drury male moths were attracted to lures containing 6Z-9S,10R-epoxy-19: H; the response was antagonized by the opposite enantiomer.Pal-this angulalis Hübner males were attracted to 9Z-6S,7R-epoxy-19:H; the opposite enantiomer was antagonistic. 6Z,9Z-19:H and 9Z-cis-6,7-epoxy-19:H and 9Z-cis-6,7-epoxy-19:H were tentatively identified in pheromone gland extracts fromAnacamptodes humaria Guenée females. In field trails, 9Z-6R,7S-epoxy-19:H proved to be the attractive enantiomer, and the response was potentiated by 6Z,9Z-19:H. Mechanisms by which unique chemical communication channels are maintained by each species are discussed.
(Z)-6-顺-9,10-环氧单烯和 (Z)-9-顺-6,7-环氧单烯的对映体富集形式，其链长 C17-20，通过Sharpless 不对称环氧化烯丙基醇中间体，随后进行 tosylation 或 halogenation 和链延伸合成。所得单不饱和环氧化物作为鳞翅目物种的性引诱剂进行了田间试验。Euchlaena madusaria Walker 雄蛾被 (Z)-6-顺-9,10-环氧壬烯 6Z-顺-9,10-环氧-19:H 的对映异构体混合物所吸引；IUPAC 名称[2α,3α(Z)]-2-戊基-3-(2-十二烯基)环氧乙烷与 6Z,9Z-19:H 组合。9Z-顺-6,7-环氧-19:H 拮抗反应。6Z,9Z-19:H 被暂定鉴定为信息素腺提取物中的化合物。Xanthotype sospeta Drury 雄蛾被含有 6Z-9S,10R-环氧-19:H 的诱饵所吸引；相反的对映异构体拮抗反应。Pal-this angulalis Hübner 雄蛾被 9Z-6S,7R-环氧-19:H 吸引；相反的对映异构体是拮抗的。6Z,9Z-19:H 和 9Z-顺-6,7-环氧-19:H 和 9Z-顺-6,7-环氧-19:H 被暂定鉴定为 Anacamptodes humaria Guenée 雌蛾信息素腺提取物中的化合物。在田间试验中，9Z-6R,7S-环氧-19:H 被证明是有吸引力的对映异构体，6Z,9Z-19:H 增强了反应。讨论了每个物种通过独特的化学通讯渠道维持的机制。
