Highly Stereoselective Synthesis of the Sex Pheromone Components of the Southern Green Stink Bug Nezara viridula (L.) and the Green Stink Bug Acrosternum hilare (Say)

Xin Chen; Levi Gottlieb; Jocelyn G. Millar

doi:10.1055/s-2000-6253

Synthesis 2000; 2000(2): 269-272
DOI: 10.1055/s-2000-6253

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Highly Stereoselective Synthesis of the Sex Pheromone Components of the Southern Green Stink Bug Nezara viridula (L.) and the Green Stink Bug Acrosternum hilare (Say)

Xin Chen^* , Levi Gottlieb, Jocelyn G. Millar

^*Department of Entomology, University of California Riverside CA 92521, USA; E-mail: jocelyn.millar@ucr.edu

Abstract

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Diastereoisomeric (Z)-(1R,2S,4S)- and (Z)-(1S,2R,4S)-epoxybisabolenes (1 and 2), sex pheromone components of the stink bugs Nezara viridula and Acrosternum hilare were synthesized stereoselectively in three steps from commercially available (-)-limonene oxide 3. Two other stereoisomers, (E)-(1R,2S,4S)- and (E)-(1S,2R,4S)-epoxybisabolenes (7 and 9) were obtained in two steps from the same starting material. The other four stereoisomers are also accessible by simply substituting (+)-limonene oxide for 3, providing short, stereoselective routes to all eight possible stereoisomers.

stink bug - pheromone - Horner-Wittig reaction

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