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

  • MPC1001F
  • Natural products
  • Total synthesis

• Graduation date

  Fall 2015

• 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.