Characterization and synthetic studies of Okundoperoxide and synthetic studies of Scyphostatin.

Abstract

The research presented in this thesis comprises two main projects: the structural characterization and synthetic studies of okundoperoxide (Chapter 4) and synthetic studies of scyphostatin (Chapter 3). In Chapter 4, I describe the characterization of a new antimalarial natural product. I also outline our biosynthetic hypothesis, which motivated us to launch a synthetic project to investigate these ideas. In Chapter 3, I describe work leading to a concise synthesis of the polar core of (+)-scyphostatin. This work included the study of a rare transformation, the vinylogous Payne rearrangement. Also, this rearrangement was found to be useful in a dynamic kinetic resolution to resolve a pair of pseudoenantiomers. Two smaller projects are discussed in the first two chapters. In Chapter 1, I discuss synthetic work directed towards preparation of an analog of kendomycin. In Chapter 2, I present reactions of various phenols with a nitrogen-based electrophile, N-phenyl-1,2,4-triazolinedione.