I. Efforts Toward the Total Synthesis of the Stemofoline Alkaloids II. Preliminary Development of a Method to Prepare 1,2-Cis-2-Acetamido-2-Deoxyglycopyranoses
Carra, Ryan
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https://hdl.handle.net/2142/84303
Description
Title
I. Efforts Toward the Total Synthesis of the Stemofoline Alkaloids II. Preliminary Development of a Method to Prepare 1,2-Cis-2-Acetamido-2-Deoxyglycopyranoses
Author(s)
Carra, Ryan
Issue Date
2008
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
Efforts to prepare the stemofoline alkaloids via total synthesis are described. Each strategy which is presented utilized a [3+2] cycloaddition of a non-stabilized azomethine ylide as a key step. These studies culminated in the first non-racemic synthesis of the fully-oxygenated tricyclic core of the stemofoline alkaloids. Furthermore, a novel synthetic method to prepare alpha-linked C2-acetamido glycoconjugates is described and preliminary results are presented.
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