Total Synthesis of Apomorphine and New Reaction Developments of Nitrogen Containing Heterocycles

Abstract

This dissertation is divided into four chapters, containing works related to the development of new methodologies towards the synthesis of nitrogen heterocycles and the development of new imine-based phosphonate reagents for olefinations, expansion and exploration of the anionic amino-Cope cascade, and the total synthesis of apomorphine. Chapter 1 explores the lead tetraacetate mediated synthesis of indoles form o-allenyl anilines via an intramolecular amino-hydroxylation. In Chapter 2, the development of new imine-based phosphonate reagents for olefination reactions was investigated allowing for the streamlined synthesis of conjugated imines for use in the anionic amino-Cope cascade. Chapter 3 focuses on efforts to expand the scope of the anionic amino-Cope reaction and displays its powerful applications to form important nitrogen heterocycles. Chapter 4 presents a new route towards the total synthesis of apomorphine with a focus on divergent total synthesis allowing for the synthesis of novel analogs.