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Application and Substrate Scope Expansion of a Unique Borylative Migration Transformation
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- Author / Creator
- Kwok, Samantha, P
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A unique borylative migration of heterocyclic enol perfluorosulfonates has been developed to access six-membered heterocyclic α-substituted allylboronates in a stereoselective and efficient manner. The synthetic utility of the allylboronate intermediates was demonstrated by a highly diastereoselective aldehyde allylboration, an enantioselective and regiodivergent Suzuki-Miyaura cross coupling and the efficient synthesis of all four stereoisomers of mefloquine. Although the mechanism of this transformation is unknown (and is currently being studied), the utility of this method still needs to be explored further. First, the application of this process towards the synthesis of all four stereoisomers of Vacquinol-1; a potential therapeutic agent for the brain cancer glioblastoma multiforme, will be described. Identified in 2014, the tested compounds were a mixture of stereoisomers. The synthetic strategy presented herein provides an efficient route to access each stereoisomer of Vacquinol-1 for the independent biological study of each compound. Moreover, analogs of Vacquinol-1 are readily accessible with the presented method. Next, efforts to expand the substrate scope of this transformation to five- and seven- membered heterocyclic substrates is disclosed. Efforts on the optimization of the amine base, chiral ligand and solvent to render the transformation enantioselective are presented.
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- Subjects / Keywords
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- Graduation date
- Spring 2016
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- Type of Item
- Thesis
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- Degree
- Master of Science
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- 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.