Synthesis and stereostructure–activity relationship of three asymmetric center pyrethroids: 2-methyl-3-phenylcyclopropyl-methyl 3-phenoxybenzyl ether and …

…, N Maruyama, K Wakasugi, Y Tanabe

Index: Nishii, Yoshinori; Wakasugi, Kazunori; Tanabe, Yoo Synlett, 1998 , # 1 p. 66 - 69

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Citation Number: 38

Abstract

2-Methyl-3-phenylcyclopropylmethyl 3-phenoxybenzyl ether 2 and cyanohydrin ester 3, a couple of pyrethroids with three asymmetric centers, were synthesized. Of each of the four diastereomers of 2 and 3, only the (1R*, 2R*, 3R*)-2a and 3a showed significant insecticidal activities. Dual sets of enantiomers [(1R, 2R, 3R)-(−)-2a and (1S, 2S, 3S)-(+)-2a] and [(1R, 2R, 3R)-(−)-3a and (1S, 2S, 3S)-(+)-3a] were synthesized through the asymmetric ...