A Short and Stereoselective Synthesis of the Sex Pheromone of

نویسندگان

  • Fabio Simonelli
  • Alfredo R.M. Oliveira
  • Francisco A. Marques
  • Davi C. Silva
چکیده

(3E,5Z)-3,5-dodecadienyl acetate was identified by Unelius C.R. et al. as the sex pheromone of the leafroller Bonagota cranaodes (Lepidoptera: Tortricidae), an economically important insect pest of apples in Southern Brazil. In order to elucidate the pheromone structure this compound was first prepared by a methodology in low stereoselectivity and yield. Recently a concise synthesis was reported by Oh D.Y. et al. based on electrophile trimethylchlorostannane-induced rearrangement of lithium 1-octynylborate as the main process. Herein we describe a short and stereoselective synthesis of this pheromone in three steps with 46,8% overall yield.

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تاریخ انتشار 1999