Klumpp, Douglas A.
M.S. (Master of Science)
Department of Chemistry and Biochemistry
Organic chemistry; Chemistry
Two areas of research are described in this thesis. The first methodology develops synthetic strategies to prepare imides. Imides possess many important properties which are utilized in applications such as high-strength polymers and bioactive molecules. This work expands upon an observation discovered during the superacid-promoted carboxamidation between ferrocenecarboxylic acid and isocyanates. By using excess TfOH solution, cyclic imides can be produced in good yields. Broadening the chemistry to aromatic carboxylic acids and aryl acetic acids required optimization of the reaction conditions, giving the product in fair to modest yield once optimized. Many cyclic imides were synthesized using this chemistry, demonstrating the scope of this reaction. The second area of research is an attempted total synthesis of the marine natural product homofascaplysin C. This class of heterocyclyes is known to have beneficial bioactive properties, making homofascaplysin C a desirable target for potential drug development. During this study, a four-step synthesis was proposed. The route produced half the target molecule in near quantitative yield before failing in a Henry reaction and forcing alternative routes. The development of the final cyclization step was done by simplifying the target molecule to pyrido[1,2-a]indole-10-carbaldehyde. Similar molecules have been produced using in our group superelectrophilic chemistry, which has been shown to cyclize triarylmethanols in good yields. Numerous R groups individually replaced one pyridine in a standard triarylmethanol structure (phenyldi(pyridin-2-yl)methanol) to study their ring closure aptitude. Additionally, if the tricyclic core was successfully formed the R group needs a known route to the aldehyde. Any positive results from these simplified studies would be used in the final ring closure of homofascaplysin C.
Schaeff, Mark N., "Synthetic methods development with electrophiles" (2017). Graduate Research Theses & Dissertations. 5199.
Northern Illinois University
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