Synthesis of (3E)-Dodecen-12-olide, a Potential Pheromone Component of the Emerald Ash Borer

Abstract

Emerald ash borer (EAB), Agrilus planipennis Fairmaire, is an invasive insect that has killed millions of ash trees in the USA and Canada. A concise synthesis of a potential EAB pheromone component, (3E)-dodecen-12-olide, using highly stereoselective Julia–Kocienski olefination as the key step, is reported.

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GRAPHICAL ABSTRACT

Keywords:

• (3E)-Dodecen-12-olide
• (3Z)-dodecen-12-olide
• emerald ash borer
• Julia–Kocienski olefination

ACKNOWLEDGMENTS

We thank Sara Carmichael for technical assistance and the Canadian Forest Service, University of New Brunswick, and National Science and Engineering Research Council of Canada (NSERC) for funding this research. All experiments reported here comply with the laws of Canada.