This thesis defense spans the scope of four projects in synthetic organic chemistry. The first is the development of a number of drug analogues for the treatment of malaria, based on the isocyanoterpene family of natural products.  The second involves the Vanderwal lab’s efforts toward the total synthesis of the Curvulamine family of natural products and attempts to develop novel pyrrole annulation chemistry. The third project is the ongoing efforts for a convergent synthesis of the arcutine family of natural products. The final project is the development of a novel strategy for diene protection to prevent catalyst relay in alkene metathesis reactions.