Bagai, Abhimanyu - Photocatalytic fluorination of benzylic C-H bonds and studies towards the synthesis of salinosporami...

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This thesis has been submitted to the Library for purposes of graduation, but needs to be audited for technical details related to publication in order to be approved for inclusion in the Library collection.
Spring 2018
Degree type: 
Department of Chemistry
Senior supervisor: 
Dr. Robert A. Britton
Thesis title: 
Photocatalytic fluorination of benzylic C-H bonds and studies towards the synthesis of salinosporamide C
Given Names: 
Fluorinated pharmaceuticals comprise nearly a quarter of the total pharmaceutical market. However, current fluorination methods and reagents lack a certain range particularly in the fluorination of C-H bonds. The first part of this thesis describes the fluorination of benzylic C-H bonds utilizing the hydrogen abstracting ability of a classic photocatalyst and a bench stable fluorine atom transfer reagent. The simple and straightforward reaction demonstrates a wide range of tolerance to functionalities and provides access to fluorinated compounds in moderate to good yield. The second part of this thesis consists of research towards the synthesis of a marine natural product, salinosporamide C, which was discovered in 2002 and has yet to be synthesized. The true activity of the compound is unknown, however its biogenetically related counterpart salinosporamide A is considered a potent 20S proteasome inhibitor. Though the total synthesis of salinosporamide C was not accomplished, an advanced intermediate was successfully synthesized and the groundwork for a successful synthesis of this natural product was completed.
photocatalysis; tetrabutylammonium decatungstate; N-fluorobenzenesulfonimide; marine natural products; salinosporamide
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