| Part I of this dissertation describes our efforts toward the total synthesis of strictamine. The synthetic strategy incorporates the use of a donor-acceptor conjugated diene, known as a Zincke aldehyde, for the rapid formation of the penultimate intermediate, deformylgeissoschizine. We explored an intramolecular oxidative enolate/indole coupling to construct the final carbon-carbon bond, and the results from preliminary experiments are discussed.;Part II focuses on the synthesis of the core of the haterumaimide family of natural products. This unique class of chlorinated, labdane diterpenes exhibits strong cytotoxic activity against P388 lymphocytic leukemia cells, as well as other cancer cell lines. Our goal was to develop a highly divergent synthesis to access several members of the haterumaimide family and non-natural analogs for further biological studies. Three strategies for the synthesis of the haterumaimides were explored. The first route aimed to develop a novel chloronium-induced π-cyclization cascade via intramolecular chloronium formation. The second strategy utilizes afuran ring as the nucleophilic terminus of a π-cyclization to form the decalin core, which serves as a latent 1.4-dicarbonyl functional group. The final strategy highlights a method for regioselective enolsilane formation to synthesize the key linear precursor required to form the decalin core, as well as a Lewis-acid mediated isomerization of vicinal dichlorides. The enantioenriched haterumaimide core was successfully synthesized using this strategy. |
