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Permanent link (DOI): https://doi.org/10.7939/R3N58CV3Q

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Synthetic methods towards the core tricyclic ring system of pradimicin A Open Access

Descriptions

Other title
Subject/Keyword
pradimicin A
natural products
carbohydrate binding agents
synthesis
organic chemistry
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Zilke, Laura Carolyn
Supervisor and department
Hall, Dennis (Chemistry)
Examining committee member and department
West, Fred (Chemistry)
Weinfeld, Michael (Oncology)
Hall, Dennis (Chemistry)
Department
Department of Chemistry
Specialization

Date accepted
2012-06-08T14:55:31Z
Graduation date
2011-11
Degree
Master of Science
Degree level
Master's
Abstract
The pradimicins are natural products that are both structurally intriguing to a synthetic chemist and possess biological activity as antifungal and antiviral agents. Our interest towards designing a synthetic route for these compounds and various analogues was sparked by the potential to produce a library of efficient carbohydrate receptors. The initial synthetic approach towards pradimicin A involved a model study of the synthesis of the core tricyclic ring system. This route featured an alkoxyallylboration, ring closing enyne metathesis and Diels-Alder cycloaddition. Chapter 2 describes the efforts towards synthesizing starting materials and the enyne metathesis precursor, which includes a mono-protected trans-diol. Chapter 3 focuses on the reaction conditions and various substrates that were tested for the ring closing enyne metathesis reaction. The optimal route found for the synthesis of the tricyclic ring system featured a one-pot palladium catalyzed cycloisomerization, Diels-Alder reaction and aromatization.
Language
English
DOI
doi:10.7939/R3N58CV3Q
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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