Enantioselective Pheromone Synthesis and Pesticide Science

After reading Silent Spring , I became interested in insect pheromones, because its application may provide us with a new and environmentally benign method of pest control. 1 was also interested in the evolving field of asymmetric synthesis. Accordingly, 1 started my enantioselective pheromone synthesis in 1973. The first work was the determination of the absolute configuration of the dermestid beetle pheromone [18]. By synthesizing the (S)-(+)-enantiomer of the pheromone from 

Subsequently in 1974,1 synthesized both the enantiomers ofe%o-brevicomin, the pheromone of the western pine beetle [19], and only the (+)-isomer was bioactive. In the case offrontahn, the (-)-isomer was the bioactive for te southern pine beetle 

Recently in 2005, we synthesized 10 g of (+)-endo-brevicomin, the minor component of the pheromone of the male southern pine beetle, Dmdroctonus frontalis [22-24]. We used lipase AK in this synthesis to desymmetrize the prochiral diol. Dr. B. T. Sullivan at the U.S. Forest Service is currently studying the practicality of the pheromone traps with a mixture of (+)-endo-brevicomin, frontaKn and a-pinene. 

I A I Only one enantiomer is bioactive, and the antipode does not inhibit the action of the pheromone. 

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