A New Asymmetric Synthesis of (S)-14-Methyl-1-Octadecene, the Sex Pheromone of the Peach Leafminer Moth

Abstract

An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth, has been efficiently achieved. A key chiral intermediate, ( R)−4-(benzyloxy)−3-methylbutanal, which has been developed as the resource chemical, can be obtained in large quantities from the steroid industry. 1,11-Undecanediol is selectively masked, and then converted into a phosphonium salt derivative, thereby effectively constructing a carbon skeleton. The target molecule is synthesized in 8 linear steps, with a 42% yield. The key characteristic of our synthesis lies in its chiral-pool strategy.