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■ Pheromone Synthesis via Organoboranes: A Stereospecific Synthesis of (E)-7-Alken-1-ols

Deevi Basavaiah*

*Wetherill Laboratory, Purdue University, West Lafayette, Indiana 47907, U.S.A.

Abstract

Borepane, obtained via hydridation of β-chloroborepane, hydroborates 1-bromo-1-alkynes cleanly to provide the β-(cis-1-bromo-1-alkenyl)borepanes. Treatment of these intermediates with sodium methoxide results in the displacement of bromine by one end of the boracycloalkyl moiety, producing the corresponding vinylboranes, containing the eight-membered borocane moiety. These intermediates, on controlled protonolysis followed by oxidation, provide the (E)-7-alken-1-ols. This process constitutes a simple, very convenient, stereospecific and general one-pot synthesis of (E)-7-alken-1-ols. Pheromones, (E)-7-tetradecen-1-ol, (E)-7-tetradecen-1-ol acetate and (E)-7-dodecen-1-ol acetate were prepared in excellent yields.