This dissertation focuses broadly on the asymmetric synthesis of various alkaloid frameworks. Chapter 1 summarizes our total synthesis of the unique alkaloid strychnochromine, and the formal asymmetric synthesis of the same. The asymmetric amination methodology we develop for this purpose is then applied to a number of different frameworks. Chapter 2 details the development of a robust strategy to synthesis the methanoquinolizidine framework, and steps to access a number of related akuammiline alkaloids.