The sex pheromone of spruce budworm (Choristoneura fumiferana Clem): synthesis of stereoisomeric mixtures of 11-tetradecenal

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University of New Brunswick


Eastern spruce budworm (Choristoneura fumiferana Clem) continues to be a major insect pest that devastates millions of hectares of spruce and fir trees in Canada. Its pheromone has successfully been used to monitor insect populations as an early warning tool for forest managers. However, its effectiveness at helping to control insect populations as part of an integrated pest management strategy has yet to be determined. The current costs associated with manufacturing the pheromone makes it economically prohibitive if large sectors of land need to be treated. In an effort to elucidate a more economical route, a stereoselective synthesis of a mixture of E/Z-11-tetradecenal has been achieved from easily accessible symmetrical aliphatic diols. Environmentally benign protecting groups and oxidation reactions were used to help increase the yield and make the developed routes viable for scale up.