Concise Synthesis of (3<i>Z</i>)-Dodecen-12-olide, Pheromone Component of the Emerald Ash Borer

<div><p></p><p>Emerald ash borer (EAB), <i>Agrilus planipennis</i> Fairmaire, is an invasive insect that has killed millions of ash trees in Canada and the USA. (3Z)-Dodecen-12-olide is a known female-produced pheromone of this insect, and a concise, three-step synthesis of a 2:1 blend of (3Z)-dodecen-12-olide and (3E)-dodecen-12-olide starting from commercially available (2-carboxyethyl)triphenylphosphonium bromide and 10-bromo-1-decene is described. The key steps in this synthesis are a lithium-salt-free Wittig reaction and an intramolecular S<sub>N</sub>2 esterification. Both of these macrocyclic lactones are behaviorally active toward EAB, and the 2:1 blend whose synthesis is described here has the potential to be a detection agent, mating disruptor, or mass trapping agent, which could be used in the control of EAB.</p> </div>

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