Organocascade Catalysis Enables a Synthesis of the Akuammiline Alkaloid Vincorine

Abstract

Three distinct organocascade catalysis strategies towards the total synthesis of the Akuammiline alkaloid vincorine are reported. The first two chapters are introductory, placing the subsequent work in appropriate context. The remaining three chapters detail our specific efforts towards this complex alkaloid, and in each chapter we are able to utilize the concept of organocascade catalysis to efficiently construct the core architecture of vincorine in a very rapid fashion. Attempts to advance each core to the natural product are highlighted, and pitfalls along the way are discussed. Finally, a radical cyclization strategy that enabled us to complete the challenging E-ring of vincorine was discovered that enabled a successful completion of the synthesis.