Photocatalytic fluorination of benzylic C-H bonds and studies towards the synthesis of salinosporamide C

Author: 
Date created: 
2018-04-18
Identifier: 
etd10646
Keywords: 
Photocatalysis
Tetrabutylammonium decatungstate
N-fluorobenzenesulfonimide
Marine natural products
Salinosporamide
Abstract: 

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.

Document type: 
Thesis
Rights: 
This thesis may be printed or downloaded for non-commercial research and scholarly purposes. Copyright remains with the author.
File(s): 
Supervisor(s): 
Dr. Robert A. Britton
Department: 
Science: Department of Chemistry
Thesis type: 
(Thesis) M.Sc.
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