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' 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.

Name thesis:degree_name

M.Sc.

Level thesis:degree_level

Masters

Discipline thesis:degree_discipline

Physics

Grantor

University of Windsor

Year dc:date.issued

1998

Author dc:creator

• Brnardic, Edward Joseph.

Advisor dc:contributor.advisor

• Green, J.

Licence

• http://creativecommons.org/licenses/by-nc-nd/4.0/

Language dc:language.iso

en_CA

Handle dc:identifier.uri

https://hdl.handle.net/20.500.14776/3513

OAI identifier oai:identifier

oai:uwindsor.scholaris.ca:20.500.14776/3513