Toward the total synthesis of Luminamicin: Construction of 14-membered lactone framework possessing versatile enol ether moiety

Article abstract of DOI:10.1016/j.tetlet.2012.03.098

Luminamicin (1) was found to exhibit selective antibacterial activity against anaerobic bacteria by our group in 1985. The concise structure of 14-membered lactone of 1 was synthesized. Construction of a versatile enol ether moiety was achieved by Stille cross coupling via hydrostanylation of the ethynyl ether, and a maleic anhydride moiety was derived from the furan constitution by the oxidation after the macrolactonization at a late-stage.