An enantioselective synthesis of the C2–C16 segment of antitumor macrolide laulimalide

An enantioselective synthesis of the C2–C16 segment of the novel antitumor agent laulimalide is described. The key steps involve a highly diastereoselective allylation, ring-closing olefin metathesis of a homoallylic alcohol derived acrylate ester, a stereoselective anomeric alkylation and an elaboration of an exo-methylene unit by a Julia olefination reaction.