Modified Ozonolytic Synthesis of 4Z-Nonen-1-ol, an Intermediate for the Synthesis of Sex Pheromones of Cotton Bollworm and Cabbage Moth, from the Cyclic Butadiene-Isoprene Codimer

Abstract

An improved procedure for preparing 4Z-nonen-1-ol, a key intermediate in the synthesis of sex pheromones of cabbage moth and cotton bollworm, from the cyclic butadiene-isoprene dimer (1-methyl-1Z,5Z-cyclooctadiene) was developed. In this procedure, the peroxide product of regioselective partial ozonolysis (0.9 equiv of O₃) of the codimer across the trisubstituted double bond is converted in one step to 9-hydroxy-5Z-nonen-2-one with NaBH(OAc)₃, the reagent that does not affect the keto groups present in the structure or formed in the process.