Synthesis of the enantiomers of 21-methyl-7-hentriacontanone and a stereoisomeric mixture of 5-acetoxy-19-methylnonacosane, candidates for the female sex pheromone of the screwworm fly, Cochliomyia hominivorax

Abstract

The enantiomers of 21-methyl-7-hentriacontanone (1), which might show weak bioactivity as the female sex pheromone of the screwworm fly (Cochliomyia hominivorax), were synthesized by starting from the enantiomers of citronellal. (±)-Citronellol was converted to a racemic and diastereomeric mixture of 5-acetoxy-19-methylnonacosane (2), which was considered to be a candidate for the female sex pheromone of C. hominivorax. Synthetic 2 exhibited no pheromone activity against male C. hominivorax.