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Synlett 1999; 1999(10): 1651-1653
DOI: 10.1055/s-1999-2903
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The First Synthesis of the Bis(indole) Marine Alkaloid Caulersin

Pilar M. Fresneda* , Pedro Molina, María Angeles Saez
  • *Departamento de Química Orgánica, Facultad de Química. Universidad de Murcia, Campus de Espinardo, E-30071, Murcia, Spain; Fax + 34 9 68 36 41 49; E-mail: pmolina@fcu.um.es
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Publication Date:
31 December 1999 (online)

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The first synthesis (seven steps) of the bis(indole) marine alkaloid caulersin is described. Construction of the central seven-membered ring is based on a Michael-type addition of the appropriate 2,3′-bis(indolyl)ketone to methylvinylketone followed by intramolecular nucleophilic substitution of the resulting 3-oxoalkylated product.

caulersin - marine alkaloid - bis(indole) - bis(indolyl)ketone - nitrene insertion