Indoloquinones, Part 7. Total Synthesis of the Potent Lipid Peroxidation Inhibitor Carbazoquinocin C by an Intramolecular Palladium-Catalyzed Oxidative Coupling of an Anilino-1,4-benzoquinone

Hans-Joachim Knölker; Wolfgang Fröhner; Kethiri R. Reddy

doi:10.1055/s-2002-20953

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Synthesis 2002(4): 0557-0564
DOI: 10.1055/s-2002-20953

FEATUREARTICLE

Indoloquinones, Part 7. [1] Total Synthesis of the Potent Lipid Peroxidation Inhibitor Carbazoquinocin C by an Intramolecular Palladium-Catalyzed Oxidative Coupling of an Anilino-1,4-benzoquinone

Hans-Joachim Knölker*, Wolfgang Fröhner, Kethiri R. Reddy
Institut für Organische Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany
Fax: +49(351)46337030; e-Mail: hans-joachim.knoelker@chemie.tu-dresden.de;

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Publication History

Received 17 December 2001
Publication Date:
28 July 2004 (online)

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Abstract

A highly efficient total synthesis of the potent lipid peroxidation inhibitor carbazoquinocin C is presented. The key-step is a palladium(II)-catalyzed oxidative cyclization of an anilino-1,4-benzoquinone to a carbazole-1,4-quinone which proceeds in up to 91% yield. Using this approach the natural product is obtained in four steps and 39% overall yield starting from aniline.

Key words

quinones - palladium catalysis - oxidative cyclization - total synthesis - carbazole alkaloids

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