Synthesis of (+)-cananodine

The goal of this graduate research project is to complete a multi-step synthesis to achieve the assembly of cananodine, a member of the guaipyridine alkaloid family, which is a biologically active molecule likely beneficial in treating liver cancer, specifically hepatocellular carcinoma (HCC). This disease is projected to affect over one million people annually by 2025 but existing therapies are expensive and not particularly effective. This synthetic route features a novel approach using an enantioselective redox-relay Heck reaction that builds off of excellent work accomplished by students in previous years who set the stage for the ultimate successful formation of the guaipyridine skeleton. Starting with simple, commercially available starting materials and using carefully chosen modern catalysts, this optically active molecule will be produced. Setting two unique stereocenters along a seven-membered carbocycle is a tricky and interesting challenge but it is imperative that progress is made in developing new compounds to change the way HCC is treated in the future.