A New Synthesis of 2-Substituted DL-Tryptophan Derivatives

Abstract
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.

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