Efficient synthesis of the Aonidiella aurantii (Mask.) sex pheromone component: (3S,6RS)-3-methyl-6-(1-methylethenyl)-9-decenyl acetate

Article abstract of DOI:10.1055/s-1995-3966

The title compound, active component of the sex pheromone of Aonidiella aurantii (California Red Scale), was synthesized in three steps starting from S-citronellyl acetate with a 30% overall yield. The key feature of the synthesis is a copper salt assisted, highly regioselective attack of the 4-butenyl bromide Grignard reagent on the γ-site of the chloroallylic system of (S)-8-chloro-3,7-dimethyl-6-octenyl acetate (8a).