Synthesis of Both the Enantiomers of 4-Methyl-1-nonanol, the Sex Pheromone of the Yellow Mealworm

Abstract

Both the enantiomers of methyl 3-methyloctanoate 2, which had been synthesized starting from methyl (R)- and (S)-3-hydroxy-2-methylpropanoate 3 in 9 steps, were converted to enantiomers of 4-methyl-l-nonanol 1, the sex pheromone of the yellow mealworm, Tenebrio molitor L. in 5 steps. As enantiomers of the pheromone 1 synthesized previously were shown to be ca. 90% e.e. or ca. 98% e.e., our synthetic sample (ca. 100% e.e.) must be a good candidate for the precise biological study.