Synthesis of cis-12-Nonadecen-9-one, cis-13-Icosen-10-one, the Pheromone of Peach Fruit Moth, and cis-15-Henicosen-11-one, the Pheromone of Douglas Fir Tussock Moth

Article abstract of DOI:10.1246/bcsj.57.2015

A convenient synthesis of cis-12-nonadecen-9-one (4a), cis-13-icosen-10-one (4b), the feromone of peach fruit moth, and cis-15-henicosen-11-one (4c), the pheromone of Douglas fit tussock moth, is described. 4a was synthesized from methyl 3-oxoundecanoate and 1-bromo-2-nonyne (2a) via 12-nonadecyn-9-one.The higher homolog 4b could be obtained from methyl-3-oxododecanoate and 2a.Similarly, 4c was prepared from methyl 3-oxotridecanoate and 1-bromo-3-nonyne (2b).