Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus(Fabricius)
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 al-dehyde.
Neoclytus acuminatus acuminatuscontact sex pheromonechiral source(S)-2-methyloxiraneasymmetric syn-thesis
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