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Title:Efforts Toward the Total Synthesis of Asparagamine A
Author(s):Epperson, Matthew Terence
Doctoral Committee Chair(s):Gin, David Y.
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
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.
Issue Date:2002
Type:Text
Language:English
Description:227 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2002.
URI:http://hdl.handle.net/2142/84078
Other Identifier(s):(MiAaPQ)AAI3070297
Date Available in IDEALS:2015-09-25
Date Deposited:2002


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