Topic
Total synthesis
About: Total synthesis is a research topic. Over the lifetime, 25578 publications have been published within this topic receiving 489319 citations.
Papers published on a yearly basis
Papers
More filters
144 citations
TL;DR: This communication delineates the first asymmetrictotal 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.
Abstract: 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.
144 citations
144 citations
144 citations
TL;DR: The total synthesis of (-)-mersicarpine was achieved in 10 steps from a known ketoester and unambiguously confirmed the reported structure of (--mersicARPine including the absolute configuration.
Abstract: The total synthesis of (-)-mersicarpine was achieved in 10 steps from a known ketoester. Our synthesis features an Eschenmoser-Tanabe-type fragmentation to synthesize an alkyne unit containing a quaternary carbon center, a facile construction of the indole skeleton via a combination of a Sonogashira coupling and a gold(III) catalyzed cyclization, as well as a one-pot process to arrange the cyclic imine and the hemiaminal moieties. Our synthesis unambiguously confirmed the reported structure of (-)-mersicarpine including the absolute configuration.
143 citations