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

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.

Automated summary

The asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of the peach leafminer moth, has been efficiently achieved, with a key chiral intermediate obtained in large quantities from the steroid industry. Selective masking and conversion into a phosphonium salt derivative were used to construct the carbon skeleton, with the target molecule synthesized in 8 linear steps and a 42% yield. The key characteristic of this synthesis lies in its chiral-pool strategy.