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An Efficient Approach to the Securinega Alkaloids Empowered by Cooperative N-Heterocyclic Carbene/Lewis Acid Catalysis


  • We thank the NSF (CHE-0619638) for an X-ray diffractometer and Prof. Gerard Parkin and Aaron Sattler for performing our crystallographic analysis. Financial support was provided by Columbia University, the NSF (Predoctoral Fellowship to A.M.E.), and the Swiss Benevolent Society of New York (Predoctoral Fellowship to D.A.W.). S.A.S. is a Fellow of the Sloan Foundation and a Cottrell Scholar of the Research Corporation for Science Advancement.


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Folding it all together: Most of the syntheses developed for the securinega alkaloid class require lengthy sequences to create their bridging butenolide domains. A novel approach uses N-heterocyclic carbenes (NHCs) and Lewis acids to forge the entire domain in a single step from appropriate precursors, showing that ynal-derived homoenolates can participate as nucleophiles in intramolecular settings (see scheme).