Synthesis of two macrolide pheromones of the rusty grain beetle, Cryptolestes ferrugineus (Stephens)

AC Oehlschlager, JW Wong, VG Verigin…

Index: Oehlschlager, Allan C.; Wong, John W.; Verigin, Victor G.; Pierce, Harold D. Journal of Organic Chemistry, 1983 , vol. 48, # 25 p. 5009 - 5017

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Citation Number: 62

Abstract

Two macrolide pheromones for Cryptolestes ferrugineus (Stephens), the rusty grain beetle, have been synthesized. Synthesis of 4, 8-dimethyl-4 (E), 8 (E)-decadienolide (1) was achieved by intramolecular alkylation of an w-bromo (pheny1thio) acetate derived from geraniol by reaction with (pheny1thio) acetyl chloride and allylic functionalization of the 8 (E)- methyl. Macrolide 1 was also synthesized by intramolecular esterification of an w-hydroxy ...

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