Studies Directed Toward the Synthesis of Streptonigrin

Abstract

The synthesis of complex pyridines has been a consistent challenge in the field of organic chemistry. Although there are many methods to accomplish this task, few methods consistently allow the synthesis of highly substituted pyridines without substantial limitations on the resulting substitution pattern. This thesis describes the synthesis of multisubstituted pyridines through both cascade cycloadditions and electrocyclic ring closure reactions through the lens of streptonigrin total synthesis. Natural product total synthesis offers both a way to test and showcase the true substrate scope of emerging synthetic methods; the pentasubstituted core of streptonigrin provides a window into the applications and limitations thereof.