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University of Illinois at Urbana-Champaign
Efforts Toward the Total Synthesis of Asparagamine A
Abstract
dc:descriptionOur efforts to complete the total synthesis of the oxytocin receptor antagonist asparagamine A are presented. A novel strategy for accessing the pyrrolizidine carbon skeleton of asparagamine A in enantiospecific fashion from L-glutamic acid has been identified. This approach utilizes an intramolecular azomethine ylide 1,3-dipolar cycloaddition reaction as the key step. Generation of the azomethine ylide species is achieved via sequential vinylogous amide O-sulfonylation and desilylation. Several strategies designed to construct the fully oxygenated aza-tricyclo[5.3.0.0 4,8]decane core are also presented.
Degree
thesis:*- 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 and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Epperson, Matthew Terence
- Contributors dc:contributor
-
- Gin, David Y.
Subjects
dc:subject × 1Rights
- Language dc:language
- eng
Identifiers
dc:identifier.*- Identifier
- (MiAaPQ)AAI3070297
- OAI identifier oai:identifier
- oai:www.ideals.illinois.edu:2142/84078