Synthetic and Pharmacological Investigations of Therapeutically Relevant N-Heterocycles

This thesis details the study of several interesting and underexplored classes of N-heterocycles with value to the field of medicinal chemistry and drug discovery. These investigations include the synthesis and biological assessment of 45 novel thalidomide analogues with potential as selective liver cancer therapeutics. Additionally, novel dirhodium(II) catalysed methodologies are explored for the synthesis of several partially saturated N-heterocycle families. Notably, this work includes new methods for accessing valuable 2- and 2,5-substituted 3,4-dehydropiperazine scaffolds. Finally, the practical utility of this novel chemistry is demonstrated in a successful diastereoselective total synthesis of the bioactive marine sponge natural product, chelonin C.