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Permanent link (DOI): https://doi.org/10.7939/R3VM4383M

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Studies Towards the Total Synthesis of MPC1001F Open Access

Descriptions

Other title
Subject/Keyword
MPC1001F
total synthesis
natural products
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Zhang, Xiangyu
Supervisor and department
Clive, Derrick L. J.
Examining committee member and department
Lowary, Todd L. (Chemistry)
Lundgren, Rylan (Chemistry)
Department
Department of Chemistry
Specialization

Date accepted
2015-08-07T11:37:59Z
Graduation date
2015-11
Degree
Master of Science
Degree level
Master's
Abstract
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.
Language
English
DOI
doi:10.7939/R3VM4383M
Rights
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. 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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