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Concise Syntheses of Insect Pheromones Using Z-Selective Cross Metathesis


  • Dr. David VanderVelde is thanked for his assistance with NMR characterization and experiments. Zachary K. Wickens and Dr. Daryl P. Allen are thanked for helpful discussion related to pheromone synthesis. This work was financially supported by the NIH (NIH 5R01GM031332-27), the NSF (CHE-1048404), and NSERC (fellowship to V.M.M.). Materia Inc. is acknowledged for the generous donation of metathesis catalyst 1.


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Very short synthetic routes to nine cis-olefin-containing pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported (see scheme). These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z olefins.