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Synlett 1997; 1997(12): 1475-1477
DOI: 10.1055/s-1997-1046
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A New Approach to the Synthesis of Aristolactams. Total Synthesis of Cepharanone A and B

Axel Couture* , Eric Deniau, Pierre Grandclaudon, Stéphane Lebrun
  • *Laboratoire de Chimie Organique Physique, Associé au CNRS (URA n° 351), Université des Sciences et Technologies de Lille I, F-59655 Villeneuve d’Ascq Cedex, France, Fax (+33) 03 20 43 65 61; e-mail Axel.Couture@univ-lille1.fr
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Publication Date:
31 December 2000 (online)

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An efficient, concise and tactically new synthesis of aristolactams is described. The key step is the aryne-mediated cyclization of an amino carbanion derived from a phosphorylated halobenzamide derivative. Horner reaction, radical cyclization and ultimate deprotection complete the synthesis of the phenanthrene lactam alkaloids. The viability of the strategy is further illustrated by the synthesis of cepharanone A and B.

phosphorylated amino carbanion - aryne-mediated cyclization - Horner-Wittig reaction - radical-mediated cyclization - aristolactams