I. Efforts Toward the Total Synthesis of (-)-Crambidine. II. Reactions of Azy(3-Me)-Containing Peptides With Thiols and Selenols

An approach to (-)-crambidine, utilizing a key [4+2] annulation reaction between a thioimidate and an electron deficient vinyl carbodiimide, has been investigated. This approach has resulted in several advanced intermediates related to (-)-crambidine, but an efficient total synthesis of (-)-crambidine has not yet been completed. Additionally, an investigation into the base-promoted thiolysis and selenolysis of Azy(3-Me)-containing peptides has been performed. While thiols were found to have low reactivity with this class of electrophilic peptide residues, two S-linked glycopeptides were successfully synthesized. Benzeneselenol was found to be highly reactive with Azy(3-Me)-containing peptides, and a variety of synthetically useful selenopeptides have been generated.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2015

Author dc:creator

• Ide, Nathan D.

Contributors dc:contributor

• Gin, David Y.

• Chemistry, Organic

Language dc:language

eng

Identifier

(MiAaPQ)AAI3242877

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/84239