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Studies Towards the Total Synthesis of MPC1001F

  • Author / Creator
    Zhang, Xiangyu
  • This thesis describes the studies towards the total synthesis of MPC1001F, a triketomonothiopiperazine natural product. In section 2.1, the first route, based on previous studies, reached the pyrrolidinone/diketopiperazine system with correct stereochemistry but did not go to completion due to the poor transformation of diketopiperazine ring synthesis by Dieckmann cyclization. Then, in section 2.2, a series of studies on the modification of the Dieckmann cyclization were conducted and finally, in section 2.3, a new route to the pyrrolidinone/diketopiperazine ring system of MPC1001F was developed and the precursor of the triketomonothiopiperazine skeleton was synthesized. This route also found the solutions of the potential problems on the MPC1001F synthesis, like electrophilic sulfenylation, diketopiperazine ring formation and hydroxyl group installation was correct stereochemistry.

  • Subjects / Keywords
  • Graduation date
    2015-11
  • Type of Item
    Thesis
  • Degree
    Master of Science
  • DOI
    https://doi.org/10.7939/R3VM4383M
  • 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
    Master's
  • Department
    • Department of Chemistry
  • Supervisor / co-supervisor and their department(s)
    • Clive, Derrick L. J.
  • Examining committee members and their departments
    • Lundgren, Rylan (Chemistry)
    • Lowary, Todd L. (Chemistry)