黑腹尼虎天牛接触性信息素的不对称合成

Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus(Fabricius)

黑腹尼虎天牛是一种危害林木与果树的蛀干害虫,其接触性信息素为(R)-9-甲基二十七烷、(R)-7-甲基二十五烷和(R)-7-甲基二十七烷.以(S)-环氧丙烷为手性源,环氧丙烷与格氏试剂的开环加成、仲磺酸酯与格氏试剂的SN2烷基化以及手性醛的Wittig偶联为关键步骤,发展了一种新的合成黑腹尼虎天牛接触性信息素的方法.

Neoclytus acuminatus acuminatus(Fabricius)is a wood-boring pest of forests and orchards.Its contact sex pheromones were(R)-9-methylheptacosane,(R)-7-methylheptacosane and(R)-7-methylpentacosane.A new and efficient synthesis of the contact sex pheromone was developed from chiral synthon of(S)-2-methyloxirane.This procedure mainly involved ring-opening reaction of(S)-2-methyloxirane,SN2 allylation of secondary tosylate and Wittig coupling of chiral aldehyde.