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Synthesis 2002(4): 0557-0564
DOI: 10.1055/s-2002-20953
DOI: 10.1055/s-2002-20953
FEATUREARTICLE
© Georg Thieme Verlag Stuttgart · New York
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
Further Information
Received
17 December 2001
Publication Date:
28 July 2004 (online)
Publication History
Publication Date:
28 July 2004 (online)
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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