Date of Award

2017

Degree Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

Abstract

Natural compounds are often used as inspiration for novel chemical structures that provide medicinal benefits to human health. The unique 3-dimentional structures of these molecules make the majority of them synthetic challenges for organic chemists. While there is great diversity among these molecules, many of these carbon-based compounds exhibit similar key structural features. One of the most common features amongst biologically active molecules is a rigid carbon ring bearing nitrogen or oxygen atoms, which are known as heterocycles. The structural rigidity of heterocycles helps properly align key interactions of the molecule with those of a specific protein, which causes the desired medicinal effect. For a molecule to be effective as a pharmaceutical its synthesis must be achievable and economically feasible. These syntheses are often accomplished by using readily available starting materials and keeping the number of synthetic steps as low as possible. The thesis research described herein will focus on the efficient construction of new heterocyclic compounds in 2-4 steps from relatively inexpensive starting materials. Specifically, we are investigating the reactivity of an underappreciated functional group, the alkylidenecyclopropane. This group is composed of a strained 3-carbon, cyclopropane ring, bearing a double bond to a carbon outside of the ring. This ring system is known to cleave in the presence of a metal catalyst, creating the opportunity to form new bonds, including those of our target heterocycles. By harnessing the high reactivity of the strained alkylidenecyclopropane system, multiple new heterocycles have been synthesized via the simultaneous formation of carbon-carbon and carbon-nitrogen bonds. The advances in this area help chemists reduce waste during their synthetic plans and provide an efficient method to create bioactive heterocycles for the advancement of human health.

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Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.

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