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Synlett 1995; 1995(6): 587-596
DOI: 10.1055/s-1995-5007
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A General Method for the Synthesis of Bridged Indole Alkaloids. Addition of Carbon Nucleophiles to N-Alkylpyridinium Salts

Joan Bosch* , M.-Lluïsa Bennasar
  • *Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain, Fax 34-3-4021896; Bitnet bennasar@farmacia.far.ub.es
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Publikationsdatum:
31. Dezember 2000 (online)

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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.

Indole alkaloids - pyridinium salts - dihydropyridines