This thesis is a summary of research conducted since September 2013 in the laboratories of Professor Robert A. Batey at the University of Toronto. The manuscript is divided into two chapters; Chapter one provides a history of trans-4,5-diaminocyclopent-2-enones, their use in total synthesis, and some related reactions. Chapter two summarizes the results obtained from two projects. The first is a project directed toward the asymmetric total synthesis of (-)-agelastatin A via chiral resolution. The second project involves the synthesis of alpha-substituted trans-4,5-diaminocyclopent-2-enones from 3-substituted 2-furaldehydes. Future work and the synthetic utility of both of these projects are also provided.M.Sc