Improved synthesis of (9Z)-9,13-tetradecadien-11-ynal, the sex pheromone of the avocado seed moth, Stenoma catenifer

Abstract

The terminal dienyne of the title compound was constructed efficiently by Sonogashira coupling of a vinyl iodide precursor with vinyl acetylene. The terminal dienyne of (9 Z )-9,13-tetradecadien-11-ynal, the sex pheromone of the avocado seed moth, Stenoma catenifer , was constructed by coupling a vinyl iodide precursor with commercially available 1-buten-3-yne with Pd catalysis, resulting in a short and efficient synthesis of the pheromone.