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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' asymmetric glycine enolate aldol condensation, Baldwin's copper catalyzed Grignards for azridine ring opening, and Jackson's 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.
Brnardic, Edward Joseph., "Synthesis of aza-tryptophan derivatives." (1998). Electronic Theses and Dissertations. 3697.