text: The synthesis of (±)-periplanone B is a prominent example of macrocyclic stereocontrol.  Periplanone B is a sex pheromone of the American female cockroach, and has been the target of several synthetic attempts.  Significantly, two reactions on the macrocyclic precursor to (±)-periplanone B were directed using only ground state conformational preferences and the peripheral attack model.  Reacting from the most stable boat-chair-boat conformation, asymmetric epoxidation of the cis-internal olefin can be achieved without using a reagent-controlled epoxidation method or a directed epoxidation with an allylic alcohol.  
  Epoxidation of the ketone was achieved, and can be modeled by peripheral attack of the sulfur ylide on the carbonyl group in a Johnson-Corey-Chaykovsky reaction to yield the protected form of (±)-periplanone B.  Deprotection of the alcohol followed by oxidation yielded the desired natural product.