The development of a template-directed C H activation strategy and its application to the diastereoselective synthesis of (±)-7-episordidin, an aggregation pheromone from the male banana weevil, Cosmopolites sordidus Germar, is reported. The key step of the synthetic route is a regioselective rhodium (II)-catalyzed diazocarbonyl C H activation reaction that simultaneously generates three of the four stereocenters present in the natural product.