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Synthesis 1995; 1995(4): 370-372
DOI: 10.1055/s-1995-3915
short paper
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A New Synthesis of 2-Substituted DL-Tryptophan Derivatives

Cesarino Balsamini, Giuseppe Diamantini, Andrea Duranti, Gilberto Spadoni* , Andrea Tontini
  • *Istituto di Chimica Farmaceutica e Tossicologica dell’Università, Piazza Rinascimento 6, I-61029 Urbino, Italy
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Publication Date:
31 December 2000 (online)

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Methyl 2-substituted N-(diphenylmethylene)-DL-tryptophanates were prepared by means of Lewis acid catalysed Michael-type addition of methyl N-(diphenylmethylene)dehydroalaninate to suitable 2-substituted indoles. Hydrolysis of these tryptophan derivatives affords the corresponding amino acids. Examples of selective deprotection of either the amino or carboxylic group are reported.

dehydroamino acids - indoles - Michael-type addition - 2-substituted tryptophans - 2-bromotryptophan synthesis