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Synthesis 1988; 1988(1): 73-76
DOI: 10.1055/s-1988-27471
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A Facile and Versatile Synthesis of 2-Substituted Tryptophans as N α-tert- Butyloxycarbonyl Derivatives

J. P. Li* , Kenneth A. Newlander, Tobias O. Yellin
  • *Smith Kline Beckman Corporation, Department of Peptide Chemistry, 1050 Page Mill Road, Palo Alto, CA 94304, USA
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Publication Date:
12 September 2002 (online)

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Diels-Alder type cycloaddition between 2-substituted indoles and ethyl α-nitrosoacrylate followed by reduction affords 2-substituted tryptophan esters. N-Protection followed by saponification furnishes the corresponding N α-protected 2-substituted tryptophans suitable for peptide synthesis. The preparation of a number of 2-substituted indoles by modified Madelung synthesis is also described.