Herein is described work culminating in the total synthesis of the proaporphine alkaloid (±)stepharine. The first chapter discusses some of the background information regarding the molecule's isolation, biological activity, and previous syntheses. Chapter 2 tells of our initial attempts at synthesizing the molecule leading to the assembly of (±)stepharine's tetrahydroisoquinoline structure. Chapter 3 recounts the completion of the synthesis using an alternate route. Also described in this chapter is the use of a CsF induced intramolecular phenolic alkylation to form (±)stepharine's spiro cross conjugated dienone structure. Experimental details and characterization are included as well. / text