Progress Toward the Total Synthesis of Upenamide

Abstract

Upenamide is a marine alkaloid natural product isolated in 2000 from the marine sponge Echinochalina sp. Protolithospongia. Spectral analysis of the marine alkaloid by the Scheuer group determined the structure upenamide to be one of two possible isomers. Due to limited supply, the overall structure and biological activity of upenamide have not been fully established and are now only available by total synthesis. Thus, chapter 1 details 3-alkylpyridine natural products and related synthetic considerations. Chapter 2 details the isolation and structural elucidation of upenamide and discusses previous synthetic approaches. Chapter 3 discusses our previous synthetic approach and synthetic efforts toward upenamide. Chapter 4 discussed the current synthetic efforts and chapter 5 outlines a strategy for the total synthesis of upenamide. Chapter 6 discusses a medicinal chemistry project discovering new small molecules for understanding the human circadian rhythm.