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Synlett 2005(16): 2469-2472  
DOI: 10.1055/s-2005-917079
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Ring-A-Substituted Tryptophan by a Palladium-Catalyzed Heteroannulation Reaction

Yanxing Jia, Jieping Zhu*
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France
Fax: +33(1)69077247; e-Mail: zhu@icsn.cnrs-gif.fr;
Further Information

Publication History

Received 15 July 2005
Publication Date:
21 September 2005 (online)

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Abstract

Coupling of substituted o-iodoanilines with methyl (S)-2-N,N-di-tert-butoxycarbonyl-5-oxo-pentanoate, derived from glutamic acid, in DMF in the presence of palladium acetate and DABCO provides substituted tryptophans in good to excellent yields.

Key words

palladium-catalyzed heteroannulation - indole synthesis - substituted tryptophan

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24

l-Try was isolated in 10% yield under Baran’s modified conditions.