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