METATHESIS SYNTHESES OF PHEROMONES OR THEIR COMPONENTS

摘要

The present invention relates to metathesis syntheses for insect sex-attractant pheromones or their components, such as E-5-decenyl acetate, themajor component of the Peach Twig Borer pheromone; (5R, 6S)-6-acetoxy-5-hexadecanolide, the mosquito oviposition attractant pheromone; E9, Z11-hexadecadienal, the pecan nut casebearer moth pheromone; 9-tetradecenylformate, an analog of the Diamondback Moth (DBM) pheromone; 11-tetradecenylacetate, the Omnivorous Leafroller (OLR) pheromone; E-4-tridecenyl acetate,the major component of the Tomato Pinworm (TPW) pheromone; E,E-8,10-dodecadienol, the Codling Moth (CM) pheromone. The syntheses preferably employa Class I-IV metathesis catalyst, entail few reaction steps, use generallycommercially available starting materials, and have relatively short processtimes. These syntheses produce good yields without the need for expensive orsophisticated equipment. The invention also provides an inexpensive route forproducing omega-haloalkenols by cross-metathesizing alpha-omega-diacetoxyalkenes and alpha-omega-dihalides to yield omega-haloalkenols, which areeasily converted into omega-haloalkanols under traditional hydrogenationmethods.