University of Illinois Urbana-Champaign

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

Ide, Nathan D.

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https://hdl.handle.net/2142/84239

Description

Title
I. Efforts Toward the Total Synthesis of (-)-Crambidine. II. Reactions of Azy(3-Me)-Containing Peptides With Thiols and Selenols
Author(s)
Ide, Nathan D.
Issue Date
2006
Doctoral Committee Chair(s)
Gin, David Y.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
Abstract
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.
Graduation Semester
2006
Type of Resource
text
Permalink
http://hdl.handle.net/2142/84239

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