Selective Syntheses of (S)-1-Methylbutyl (E)-2,4-Dimethyl-2-Pentenoate, an Aggregation Pheromone Component of Rhyzopertha dominica, and of (E)-2-Butyl-2-Octenal, an Alarm Pheromone Component of Oecophylla longinodavia 2-Substituted 1-Sdlyl-1-Stannylethenes 1)

Abstract

Two easily available stereodefined organobimetallic compounds, i.e. (Z)-1-trimethylsilyl-1-trimethylstannyl-3-rnethyl-1-butene, (Z)-1a, and (Z)-1-tri-methylsilyl-1-tributylstannyl-1-heptene, (Z)-12, which serve as direct precursors to reagents which are synthetic equivalents of the 1-alkene 2d¹ synthon 20, have been used as key intermediates in selective and efficient syntheses of two insect pheromone components, i.e. enantiomerically pure (S)-1-methylbutyl (E)-2,4-dimethyl-2-pen-tenoate (dominicalure-2), (SXE)-10, and (E)-2-butyl-2-octenal, (E)-11, respectively.