Enantioselective total synthesis of lycoposerramine W through late-stage nitrogen deletion

A concise total synthesis of lycoposerramine W was accomplished in 10 steps (longest linear sequence) through the union of two fully elaborated piperidine and tetrahydroquinoline fragments, which were prepared by remote biocatalytic C–H oxidation and metal-catalyzed oxidative annulation, respectively. Several C–C bond forming reactions were surveyed for the key fragment coupling, which ultimately identified a nitrogen deletion strategy as the only feasible solution to the problem. This work highlights the benefits of incorporating modern synthetic methodologies in streamlining access to complex molecules.