A practical synthesis of (all-Z)-eicosa-3,6,9,12-tetraene, a pheromone component isolated from emerald moths

A short and practical synthesis of (all-Z)-eicosa-3,6,9,12-tetraene, a component of the emerald moth pheromone is reported. Two different methodologies are used both starting with the natural polyunsaturated fatty acid (all-Z)-eicosa-5,8,11,14,17-pentaenoic acid (EPA). The methodology can be used for the syntheses of a homologous series of analogues of the pheromone that may be practical for analytical purposes of similar natural products.