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Permanent link (DOI): https://doi.org/10.7939/R3M39W

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Intramolecular conjugate displacement for making carbocycles and studies on the total synthesis of MPC1001 Open Access

Descriptions

Other title
Subject/Keyword
Baylis-Hillman
MPC1001
ICD
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Wang, Lihong
Supervisor and department
Clive, Derrick L.J. (Chemistry)
Examining committee member and department
Back, Thomas G. (Chemistry, University of Calgary)
Weinfeld, Michael (Oncology)
Li, Liang (Chemistry)
Clive, Derrick L.J. (Chemistry)
Lowary, Todd L. (Chemistry)
Vederas, John C. (Chemistry)
Department
Department of Chemistry
Specialization

Date accepted
2012-06-08T11:40:21Z
Graduation date
2011-11
Degree
Doctor of Philosophy
Degree level
Doctoral
Abstract
The first chapter of this thesis describes methodology on an all-carbon intramolecular conjugate displacement between a carbon nucleophile and a Morita-Baylis-Hillman adduct for making carbocyclic skeletons. The reaction scope was examined with different electron-withdrawing groups, types of carbon nucleophile and leaving groups. The study demonstrated that this transformation is a convenient and effective way of constructing carbocycles, including some synthetically challenging structures. The mechanism of this transformation was probed by experiments designed to trap a possible anionic species of a non-concerted pathway. The second part of my thesis describes studies towards the total synthesis of the natural product MPC1001, which is a potential anti-tumor agent. Effort was focused on inventing a way of installing a disulfur bridge in a stereo-controlled manner. Difficulties were encountered for thiol deprotection, as attempted removal of many known thiol-protecting groups gave either no reaction or loss of the sulfur, possibly expelled by the nitrogen on the same carbon. Therefore, a new protecting group for thiols was designed, which could be deprotected under mild conditions. Although this protecting group allowed smooth deprotection with one specific reagent, additional problems prohibited carrying the research further using this group. A new route for installing the disulfide bridge was conceived and is still under examination.
Language
English
DOI
doi:10.7939/R3M39W
Rights
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.
Citation for previous publication
Lihong Wang, American Chemical Society (2009)Lihong Wang, American Chemical Society (2011)

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File title: Thesis 2011-09-26
File author: Lihong Wang
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