A New Synthesis of 2-Substituted DL-Tryptophan Derivatives

Cesarino Balsamini; Giuseppe Diamantini; Andrea Duranti; Gilberto Spadoni; Andrea Tontini

doi:10.1055/s-1995-3915

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

Abstract

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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

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