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Studies towards the total synthesis of CP-225,917 and CP-263,114 Open Access


Other title
Total synthesis
Type of item
Degree grantor
University of Alberta
Author or creator
Malihi, Farzad
Supervisor and department
Clive, Derrick
Examining committee member and department
Dr. L. Li, Department of Chemistry
Dr. D. L. J. Clive, Department of Chemistry (Supervisor)
Dr. J. C. Vederas, Department of Chemistry
Dr. D. J. Burnell, Dalhousie University (External Examiner)
Dr. T. L. Lowary, Department of Chemistry
Dr. M. Gänzle, Department of Agriculture, Food & Nutritional Science
Department of Chemistry

Date accepted
Graduation date
Doctor of Philosophy
Degree level
This thesis describes advanced model studies directed to the synthesis of CP- 225,917 and CP-263,114, complex natural products that have been shown to inhibit enzymes that are involved in cholesterol biosynthesis and in the development of many cancers. A route was devised to the functionalized pentacyclic skeleton of these natural products. The most advanced intermediate carries the essential substituents for construction of the anhydride subunit and one of the two olefinic arms that are present in both compounds. The approach used involves a Diels- Alder reaction, an unusual fragmentation of a strained [2.2.1]bicycle and the method of intramolecular conjugate displacement, which had previously been developed in this laboratory. A number of model studies were carried out to identify a procedure for introducing the last carbon required for the anhydride subunit and, based on these studies, that carbon was introduced via the use of a [2,3]-Wittig rearrangement.
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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File title: 00 Farzad Thesis prefatory pages FINAL 2012 August 22d, Septemebr 23a
Page count: 58
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