Open Access Thesis
Master of Science (MS)
Harriet Lindsay, PhD, Chair
Arthur Howard, PhD
Timothy Friebe, PhD
Pyrrolizidine alkaloids are a large class of natural products whose members exhibit a variety of biological properties including potential applications toward the treatment of cancer, diabetes, and viral infections such as HIV. In addition, some of these compounds exhibit insect antifeedant activity, and so have potential applications in the agricultural industry for the protection of crops.
For these reasons, we were interested in developing a method to form the bicyclic alkaloid core that could be functionalized to generate many pyrrolizidine alkaloids. Specifically, our goal was to synthesize the pyrrolizidine B-ring by a novel McMurry cyclization strategy (Scheme 1). The synthesis of the McMurry reaction precursors and efforts at optimizing the key McMurry reaction will be described.
Tuluoglu, Fatmagul, "Synthesis of the bicyclic core of pyrrolizidine alkaloids" (2009). Master's Theses and Doctoral Dissertations. 247.