Date of Award

2013

Degree Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Graduate Group

Chemistry

First Advisor

Amos B. Smith, III

Abstract

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.

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