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Permanent link (DOI): https://doi.org/10.7939/R3J67972C

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Studies towards total synthesis of MPC1001F - a triketopiperazine- dihydrooxepin natural product Open Access

Descriptions

Other title
Subject/Keyword
Conjugate addition elimination
Dieckmann type cyclization
Total synthesis
Diketopiperazine dihydrooxepin
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Bhattacharyya, Dipanjan
Supervisor and department
Clive, D. L. J. (Chemistry)
Examining committee member and department
Dmitrienko G. (University of Waterloo, Chemistry, External Examiner)
Lowary, Todd L. (Chemistry)
West, Frederick G. (Chemistry)
Narain, Ravin (Chemical and Materials Engineering)
Li, Liang (Chemistry)
Department
Department of Chemistry
Specialization

Date accepted
2012-09-10T10:10:23Z
Graduation date
2013-06
Degree
Doctor of Philosophy
Degree level
Doctoral
Abstract
The thesis describes synthetic studies towards MPC1001F, a triketopiperazine-dihydrooxepin natural product. Another related member of this class of natural products is MPC1001 with an epidithiodioxopiperazine core and potent antitumor activity. Our goal was to construct the molecular skeleton of the comparatively simpler MPC1001F first so that the knowledge gained during this project can be applied to the synthesis of the more complex MPC1001. None of these MPC natural products have yet been synthesized. An enantioselective synthesis of the tricyclic core of MPC1001F is discussed first, by a route which followed the strategy on a related core, already established in our group. The main synthetic challenges encountered in this route are discussed. These involved oxidation of an alcohol without epimerization next to the resulting aldehyde, oxidation of an alcohol in the presence of selenium, and construction of a tetrahydrooxepin ring via a conjugate addition-elimination process. An insurmountable obstacle in this route led us to explore a different strategy. In the next section, several unsuccessful approaches towards the core, starting from already-synthesized intermediates from the first route, are described. Finally, I designed a new short enantioselective sequence towards the core structure which is shown in the third section of this thesis. The synthesis of the tricyclic core has been achieved following this new strategy. The last few steps to the fully functionalized core are still being studied.
Language
English
DOI
doi:10.7939/R3J67972C
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.
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