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Synlett 1992; 1992(7): 601-602
DOI: 10.1055/s-1992-22020
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Diels-Alder Reaction of a 2-Vinyltryptamine: An Approach to the Echitamine Ring System

Jean Lévy* , Janos Sapi, Jean-Yves Laronze, Daniel Royer, Loïc Toupet
  • *Laboratoire de Transformations et Synthèse de Substances Naturelles, associé au CNRS, Université de Reims-Champagne-Ardenne, Faculté de Pharmacie, 51 rue Cognacq Jay, F-51096 Reims, France
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Publication Date:
08 March 2002 (online)

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Diels-Alder cyclization of N-benzyl-N′-methoxycarbonyl-2-vinyltryptamine (5) with dimethyl maleate yielded a tetracyclic compound 7 [9-benzyl-3,4,10-trimethoxycarbonyl-1,2,3,4-tetrahydro-9a, 4a-(iminoethano)-9H-carbazole] with structural features closely related with those of the indole alkaloid echitamine (4).