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Synlett 2000; 2000(8): 1190-1192
DOI: 10.1055/s-2000-6746
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The First Synthesis of the Bis(indole) Marine Alkaloid Rhopaladin D

Pilar M. Fresneda* , Pedro Molina, Miguel A. Sanz
  • *Departamento de Química Orgánica, Facultad de Química. Universidad de Murcia, Campus de Espinardo, E-30071, Murcia, Spain; Fax + 34 968 36 41 49; E-mail: pmolina@fcu.um.es
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Publication Date:
31 December 2000 (online)

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The first synthesis (six steps) of the bis(indole) alkaloid Rhopaladin D isolated from the marine tunicate Rhopalaea sp. is described. The key step, construction of the central imidazolinone ring, is based on the aza-Wittig reaction of the iminophosphorane derived from the α-azido-β-(3-indolyl)propenamide and indolyl-3-glyoxylyl chloride in the presence of polymer-supported BEMP as a base.

rhopaladins - marine alkaloid - bis(indole) - aza-Wittig reaction - iminophosphorane