Total Synthesis of (–)-Invictolide

Abstract

A convergent approach to the total synthesis of (–)-invictolide, a component of the queen recognition pheromone of Solenopsis­ invicta, is described. Key steps involve the desymmetrization of a bicyclic olefin with Brown’s chiral hydroboration, C–C bond formation, 1,3-syn reduction, and oxidative lactonization of a 1,3,5-triol with TEMPO/PhI(OAc)₂.

Key words

pheromones - desymmetrization strategy - syn-1,3-reduction - oxidative lactonization

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