Date of Award


Degree Type


Degree Name

Doctor of Philosophy (PhD)

Graduate Group


First Advisor

Amos B. Smith, III


In this dissertation, three successful applications of Type II Anion Relay Chemistry (ARC), a versatile multi-component union tactic, are described.

Part 1: An effective, general protocol for the Diversity-Oriented Synthesis (DOS) of 2,4,6-trisubstituted piperidine congeners has been designed and validated. The successful strategy entails a modular approach to all possible stereoisomers of a selected piperidine scaffold, exploiting Type II Anion Relay Chemistry (ARC), followed in turn by intramolecular SN2 cyclization, chemoselective removal of the dithiane moieties and carbonyl reductions.

Part 2: A highly convergent synthesis of (-)-secu'amamine A has been achieved by exploiting a highly efficient Type II Anion Relay Chemistry (ARC) tactic to provide the full carbon and nitrogen skeleton with requisite functionalities in a single-flask.

Part 3: One-step access to diverse carbobicycles utilizing Type II ARC envolving Aldol-Brook Rearrangement-Cyclization Cascade reaction was proposed and validated.

Files over 3MB may be slow to open. For best results, right-click and select "save as..."