Date of Completion
Honors Thesis - Campus Access
Tina Choe, Ph.D.
Photochemical decarbonylation reaction of ketones has been the focus of much interest since its discovery in the early 1900's. The mechanism of this reaction involves the loss of CO by a sequential cleavage of two sigma bonds via the Norrish Type 1 mechanism. My thesis work was to synthesize bridged ketones and use them to develop the solid-state photodecarbonylation reaction. This reaction provides opportunities to synthesize complex bicyclic compounds, carbohydrate derivatives, and functionalized cyclopentane systems from corresponding ketones. Conducting the reaction in the solid state not only eliminates the need for organic solvents but it can provide stereochemical selectivities and specificities that are difficult to achieve in standard solution state chemistry. The synthesis of these bridged ketones also provided a number of chemical intermediates, which were screened inhibition potential towards the aggregation of amalydogenic proteins like Aβ-42 and IAPP. Screening of compounds was carried out using Thioflavin T and fusion EGFP-Aβ-42 assays.
Goodman, C. Guy, "The Synthesis of Bicyclic Ketones as a method of Studying the Photochemical Decarbonylation Reaction and the Search for Novel IAPP and Aβ-42 Aggregation Inhibitors" (2011). Honors Thesis. 89.