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The straightforward synthesis of two long-chain diene ketals, ( Z ,  Z )-11, 11-dimethoxy-6, 9-heneicosadiene and 2-  n  decyl-2-(( Z ,  Z )-1, 4-decadienyl)-1, 3-dioxolane, is described. These two ketals are synthetic propheromones, or pheromone precursors, of the whitemarked tussock moth (WMTM,  Orgyia leucostigma  (J. E. Smith) (Lepidoptera: Erebidae)), whose unstable female-produced sex pheromone component, ( Z ,  Z )-6, 9-heneicosadien-11-one, lasts only 1-2 days in traps in the field. The two propheromones were synthesized by terminal alkyne / propargylic bromide couplings, facilitated by cesium carbonate, which assembled the 21-carbon chains with skipped diynes. Semi-reduction of the diynes gave the requisite dienes. These two diene acetals were then formulated into lures which converted them  in situ  into the attractive ( Z ,  Z )-6, 9-heneicosadien-11-one. The performance of these lures is briefly described.&#x0D;

canadian journal of chemistry

A new synthesis of (Z,Z)-11,11-dimethoxy-6,9-heneicosadiene and 2-((Z,Z)-1,4-decadienyl)-2-ndecyl-1,3-dioxolane, precursors of (Z,Z)-6,9-heneicosadien-11-one, a pheromone component of the whitemarked tussock moth, Orgyia leucostigma (J.E. Smith) (Lepidoptera: Erebidae)