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. Keywords Hyphantria cunea; synthesis of pheromone; Sharpless asymmetric epoxidation; alkylative epoxide rearrangement 美国白蛾(Hyphantria cunea)是一种严重危害农、林 业的世界性检疫害虫 [1][2] , 具有寄主范围广、扩散速度 快、适应性强、难于防治等特点 [3][4] . 美国白蛾性信息素 是由成虫雌蛾分泌、释放的微量化学物质, 具有引诱雄 虫的生理活性 [5][6] , 可用于虫情监测 [7] 与诱捕雄虫 [8][9] . 利用昆虫性信息素进行农业害虫的绿色防控, 具有用量 少、选择性强、不产生抗性、对寄主植物与环境安全等 诸多优势, 是最具有应用前景的新技术 [10][11] .