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Theses and Dissertations

Indolizidine alkaloids and asymmetric synthesis of carbocycles Open Access


Other title
ntramolecular conjugate displacement reactions (ICD)
Diels-Alder reactions
assymmetric synthesis
Myers asymmetric alkylation
conjugate additions
asymmetric carbocycle synthesis
Type of item
Degree grantor
University of Alberta
Author or creator
Wingert, David Alexander
Supervisor and department
Clive, Derrick L.J. (Chemistry)
Examining committee member and department
Bergens, Steven (Chemistry)
West, Fred (Chemistry)
Mercer, John (Oncology)
Clive, Derrick L.J. (Chemistry)
Lowary, Todd (Chemistry)
Department of Chemistry

Date accepted
Graduation date
Doctor of Philosophy
Degree level
The first chapter of this thesis describes the development of an asymmetric route to the core structure of the indolizidine alkaloids and its application to the total synthesis of (+)-ipalbidine, a member of this compound class. The initial approach was designed to use the intramolecular conjugate displacement (ICD) reaction developed in this group as the method to form the bicyclic core structure of these compounds. Some limitations of this useful method were uncovered under these circumstances, and a different approach was required to carry out the synthesis. The indolizidine structure was formed by use of a conjugate addition and the total synthesis of (+)-ipalbidine was completed. The second chapter describes the expansion of the all-carbon ICD reaction previously developed by this group for carbocyclic ring formation. The goal was to install a pendant chain in an asymmetric fashion onto the carbocycle precursors and then form the rings using the ICD reaction. The strategically placed pendant chain could then be manipulated and utilized as a handle to elaborate the carbocyclic intermediates into more complex structures. This chapter describes (a) the use of the Myers asymmetric alkylation reaction as an installation method for the pendant chain, (b) the production of the asymmetrically substituted carbocycles via the ICD reaction and (c) our efforts to elaborate these intermediates into more complex compounds.
Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
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