| This document contains the reported work on three projects, each with different goals. Chapter one describes the diastereoselective synthesis of a series of non-natural products via imine-anhydride reactions to be used as molecular probes to determine the properties of toxin expression in poison dart frogs. Chapter two contains the history of, and work towards, the total synthesis of nakadomarin A. New reactions developed in this section include magnesium enolate formation from aryl sulfoxides, and subsequent Michael/Diekmann cyclization. Other reactions include the first direct allylation of a nitrile substituted gamma-lactam the formation of a unique heterotriquinane. Chapter three focuses on the reassignment, and studies towards the total synthesis of, the alkaloid jamtine. This work also contains an appendix, which describes the methods used in both the computational work and the X-ray crystallography that is reported in chapter two. |
