美国白蛾性信息素(3Z,6Z,9S,10R)-9,10-环氧-3,6-二十一碳二烯的不对称合成

Asymmetric Synthesis of(3Z,6Z,9S,10R)-9,10-Epoxy-3,6-heneicosadiene,Sex Pheromone Component of Hyphantria cunea

美国白蛾是一种严重危害农、林业的世界性检疫害虫,其性信息素的主要活性成分为(3Z,6Z,9S,10R)-9,10-环氧-3,6-二十一碳二烯.以1-溴十一烷为起始原料,经卤代烃的亲核取代、醋酸镍/硼氢化钠催化氢化、Sharpless不对称环氧化、高氯酸开环、烷基环氧重排(包括环氧开环与碳酸钾催化关环)等11步反应,总收率为14%,发展了一种新的合成美国白蛾性信息素主要活性成分的方法.

Hyphantria cunea is an important worldwide pest due to its destructiveness to the crops and trees.The main active component of its sex pheromone is(3Z,6Z,9S,10R)-9,10-epoxy-3,6-henicosadiene.A new synthesis of the sex pheromone from 1-bromoundecane was developed.The procedure includes 11 steps,and the overall yield is 14%.Furthermore,nucleophilic substitution of alkyl halide,partial hydrogenation with nickel boride,Sharpless asymmetric epoxidation,ring opening with HClO_(4),and alkylative epoxide rearrangement(invovling the ring opening of terminal epoxide and the ring-closure with K_(2)CO_(3))are crucial steps.