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

doi:10.1055/s-2005-869977

PAPER

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;

Abstract

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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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