Asymmetric synthesis of. gamma.-lactones. A facile synthesis of the sex pheromone of the Japanese beetle

MM Midland, NH Nguyen

Index: Midland, M. Mark; Nguyen, Nhan H. Journal of Organic Chemistry, 1981 , vol. 46, # 20 p. 4107 - 4108

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Citation Number: 69

Abstract

Sir: Chirality often plays a critical role in the biological activity of molecules. This phenomenon is particularly important for the sex pheromone produced by the female Japanese beetle, Popillia japonica, which has been identified as (R)-(-)-(Z)-5-tetradecen-4- olide. As little as 1% of the S, Z isomer can significantly reduce the response of male beetles to the R, Z isomer. The R and S enantiomers of the pheromone were originally prepared ...