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Hartrampf, Felix W. W.; Furukawa, Takayuki; Trauner, Dirk (2017): AConia-Ene-Type Cyclization under Basic Conditions Enables an Efficient Synthesis of (-)-Lycoposerramine R. In: Angewandte Chemie-international Edition, Vol. 56, Nr. 3: S. 893-896
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An enantioselective total synthesis of the Lycopodium alkaloid lycoposerramineR is presented. It relies on a base-mediated cyclization that resembles the Conia-ene reaction of ynones and gold-catalyzed variants thereof. Thus, hydrindanones and other functionalized ring systems bearing an exocyclic alkene can be rapidly accessed at room temperature without noble metal catalysis or substrate preactivation.