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

  • Author / Creator
    Malihi, Farzad
  • 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.

  • Subjects / Keywords
  • Graduation date
    2012-09
  • Type of Item
    Thesis
  • Degree
    Doctor of Philosophy
  • DOI
    https://doi.org/10.7939/R3N396
  • License
    This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.
  • Language
    English
  • Institution
    University of Alberta
  • Degree level
    Doctoral
  • Department
    • Department of Chemistry
  • Supervisor / co-supervisor and their department(s)
    • Clive, Derrick
  • Examining committee members and their departments
    • Dr. D. L. J. Clive, Department of Chemistry (Supervisor)
    • Dr. M. Gänzle, Department of Agriculture, Food & Nutritional Science
    • Dr. T. L. Lowary, Department of Chemistry
    • Dr. J. C. Vederas, Department of Chemistry
    • Dr. L. Li, Department of Chemistry
    • Dr. D. J. Burnell, Dalhousie University (External Examiner)