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

  • CP-263,114
  • Total synthesis
  • CP-225,917

• Graduation date

  Fall 2012

• 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.