Angewandte Chemie International Edition · 2014 · 131 citations · 47 references
PharmacyChemistryMedicinal ChemistryDrug DiscoveryOrganic ChemistrySynthetic Medicinal ChemistryAlkaloid BiosynthesisMedicinal PlantsNatural Product Drug DiscoveryOrganic SynthesisRetrosynthetic AnalysisIndole AlkaloidsIndole ChemistryNatural Product SynthesisNatural Product Total SynthesisOxidative CouplingOxidative Coupling ReactionsPiperidine ChemistryPlant Alkaloids
Abstract Aspidophylline A belongs to the akuammiline alkaloid family, the members of which possess intriguing cagelike structures and diverse biological activities. Herein we report a 15‐step synthesis of this alkaloid from conveniently available starting materials. The key elements of the synthesis include an intramolecular oxidative coupling to create the tetracyclic furoindoline motif of the natural product and a [Ni(cod) 2 ]‐mediated cyclization to install its piperidine ring.
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Phil S. Baran, Jeremy M. Richter · Journal of the American Chemical Society · 2004 · 249 citations
Amy B. Dounay, P. G. Humphreys, Larry E. Overman et al. · Journal of the American Chemical Society · 2008 · 214 citations · Full text