Asymmetric Synthesis and Biological Activity of Contact Pheromone of Western Flower Thrips, Frankliniella occidentalis

Western flower thrips, <i>Frankliniella occidentalis</i>, is a serious worldwide pest of agriculture and horticulture, and its contact pheromone is 7-methyltricosane. Two enantiomers of 7-methyltricosane were synthesized for the first time. The centra of our strategy were chiral auxiliaries to introduce stereocenter, and Wittig coupling to connect two blocks. The overall yields of our synthesis were 29-30% with seven steps. The electroantennogram (EAG) and the contact behavioral responses revealed that (<i>R</i>)-, (<i>S</i>)- and racemic 7-methyltricosane were separately bioactive, and the racemate was the most bioactive in the male arrestant activity and the female EAG test. This result provides valuable insights, showing that the racemate could be used for the support of the control of western flower thrips, which could be more easily prepared relative to more expensive enantiopure pheromone.