Efforts Toward the Total Synthesis of Asparagamine A
Epperson, Matthew Terence
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https://hdl.handle.net/2142/84078
Description
Title
Efforts Toward the Total Synthesis of Asparagamine A
Author(s)
Epperson, Matthew Terence
Issue Date
2002
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
Our 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.
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