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Synthesis 2005(12): 1959-1966  
DOI: 10.1055/s-2005-869977
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Indolo[2,3-a]pyrrolo[3,4-c]carbazoles by Oxidative Cyclization of Bisindolylmaleimides with a Rhodium(III)-Copper(II) Catalytic System

Bernhard Witulski*, Torsten Schweikert
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Correnstr. 40, 48143 Münster, Germany
Fax: +49(251)8336501; e-Mail: witulski@uni-muenster.de;
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Publikationsverlauf

Received 12 January 2005
Publikationsdatum:
24. Juni 2005 (online)

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Abstract

A novel catalytic protocol for the synthesis of a series of indolo[2,3-a]pyrrolo[3,4-c]carbazoles based on the bimetallic system RhCl3·3H2O and Cu(OAc)2·H2O in the presence of molecular oxygen was investigated. The method was applied to the synthesis of the glycosidated fluoroindolocarbazole 3 that was recently isolated as a metabolite from feeding experiments of Saccharothrix aerocolonigenes ATCC 39243 with fluorotryptophanes.

Key words

glycosides - rebeccamycin - catalysis - rhodium - copper

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