Natural products have a rich history of providing attractive fragments as well as lead compounds for the development of valuable therapeutic agents. Despite their utility, employment of these terrestrial compounds is frequently hindered by scarcity, architecturally complexity or the combination thereof. Therefore, the total synthetic synthesis of complex natural products, which incorporate innovative and efficient synthetic designs provide streamlined access to these compounds and their derivatives. Furthermore, studies toward the synthesis of complex natural products and their analogs inspire the development of novel, expeditious, and practical methods that are essential for the construction of new pharmaceuticals and stimulating organic compounds.

The first part of this dissertation focuses on the synthetic studies directed toward the synthesis of (--)-galanthamine. The focal point of this effort is to explore and showcase the use of the carbon-hydrogen bond as a practical disconnection in a synthesis design. Through these studies, a series of synthetically challenging C-H functionalization methods have been developed. In conjunction with classic transformations in organic synthesis these methods have enabled a concise synthesis plan towards our natural product target.

The second part of this dissertation describes the development of a general alpha fluorination of N-acyl oxazolidinones via Group IVa metal enolates by an electrophilic method. The main goal of this effort was to access valuable fluorinated organic material in an economical, experimentally simple, functional group compatible, and highly selective manner.