Date of Award
1998
Publication Type
Master Thesis
Degree Name
M.Sc.
Department
Physics
Keywords
Chemistry, Organic.
Supervisor
Green, J.
Rights
info:eu-repo/semantics/openAccess
Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-No Derivative Works 4.0 International License.
Abstract
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.
Recommended Citation
Brnardic, Edward Joseph., "Synthesis of aza-tryptophan derivatives." (1998). Electronic Theses and Dissertations. 3697.
https://scholar.uwindsor.ca/etd/3697