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The napyradiomycins are an intriguing family of halogenated natural products with activity against several tumor cell lines as well as some of the worst bacterial strains known to humanity, including methicillin-resistant Staphylococcus aureas and vancomycin-resistant strains of Enterococcus faecium. This communication delineates the first asymmetric total synthesis of (−)-napyradiomycin A1 by a strategy that features a two-step total synthesis of flaviolin, the first highly asymmetric halogenation of a simple alkene, and a Johnson−Claisen rearrangement that generates a quaternary carbon next to a glucal-like oxygen.