Key steps in the convergent enantioselective synthesis of the cytotoxic natural product cylindramide are tandem Michael addn./electrophilic trapping reactions, Sonogashira coupling, Julia-Kocienski olefination, and macrocyclization. For example, the Sonogashira coupling of pentalene I with iodoacrylate II followed by Julia-Kocienski olefination with sulfone III gave an intermediate which underwent macrocyclization. Formation of the tetramic acid completed the synthesis.