摘要/Abstract

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.
关键词: 美国白蛾, 信息素合成, Sharpless不对称环氧化, 烷基环氧重排
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 HClO₄, and alkylative epoxide rearrangement (invovling the ring opening of terminal epoxide and the ring-closure with K₂CO₃) are crucial steps.
Key words: Hyphantria cunea, synthesis of pheromone, Sharpless asymmetric epoxidation, alkylative epoxide rearrangement


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