Magee, Kurtis Michael. “Total Synthesis of 20-F4t-Neuroprostane”. MS, Boston College, 2011. http://hdl.handle.net/2345/2423.
Chapter 1: Oxidative Stress. An overview of oxidative stress and its impact on human health. Various reactive oxygen species and cellular antioxidant defenses are also summarized. Chapter 2: Neuroprostanes. After a survey of fatty acids and their nomenclature, this chapter discusses lipid peroxidation as one of the most significant consequences of oxidative stress in vivo. Lipid metabolites that serve as biomarkers for human diseases are also examined. Chapter 3: First Total Synthesis of 20-F4t-Neuroprostane. Beginning with a brief review of previous neuroprostane syntheses and the Snapper lab's approach to the isoprostanes, the final chapter presents our total synthesis of 20-F4t-neuroprostane. The key steps in the synthesis involve a modified ring-opening cross-metathesis/cross- metathesis procedure and a one-pot asymmetric double Wittig olefination.