This study also shows how the development of methodology advances synthetic efficiency; methodological improvements included scalable Pd-catalyzed ketone-to-enone dehydrogenation, Pd-catalyzed oxidative enone β-stannylation, Pdcatalyzed epoxyketone rearrangement, and use of a stannane coupling partner in the Liebeskind pyridine synthesis. Furthermore, strategic deployment of modern computational techniques helped direct our total synthesis campaigns through structural reassignment by NMR calculations and feasibility assessments of proposed transformations.