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A General Method for the Synthesis of Bridged Indole Alkaloids. Addition of Carbon Nucleophiles to N-Alkylpyridinium Salts
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1995
Year
Bioorganic ChemistryIndole RingNatural SciencesStabilized Carbon NucleophilesOrganic ChemistryBridged Indole AlkaloidsStereoselective SynthesisChemistryGeneral MethodHeterocycle ChemistryPharmacologyCarbon NucleophilesSynthetic ChemistryEnantioselective SynthesisNatural Product Synthesis
The methodology based on the nucleophilic addition of stabilized carbon nucleophiles to N-alkylpyridinium salts constitutes a powerful tool for the synthesis of bridged indole alkaloids belonging to a variety of structural types, either tetracyclic (as vinoxine and ervitsine) or pentacyclic, in the latter case after closure of the tryptamine chain by cyclization upon the indole ring.