Synthesis of aza-tryptophan derivatives.

The preparation of racemic 7-azatryptophan from 7-azaindole has been accomplished. The aldol condensation of 1-tert-butoxycarbonyl-3-formyl-7-azaindole with methyl hippurate installed the carbon framework necessary for the intended product. Subsequent deoxygenation and deprotection of the indole, ring, and the amino and acid functional groups yielded racemic 7-azatryptophan A variety of attempts to synthesize the enantiomerically pure form of 7-azatryptophan were considered. Of those Evans\u27 asymmetric glycine enolate aldol condensation, Baldwin\u27s copper catalyzed Grignards for azridine ring opening, and Jackson\u27s coupling reaction with aryl iodides were employed. Unfortunately though, all methods proved unrewarding. Paper copy at Leddy Library: Theses & Major Papers - Basement, West Bldg. / Call Number: Thesis1998 .B76. Source: Masters Abstracts International, Volume: 39-02, page: 0513. Adviser: James Green. Thesis (M.Sc.)--University of Windsor (Canada), 1998