Thesis advisor: Marc L. Snapper / Chapter 1: A review of Shapiro reactions as a coupling strategy in natural product total synthesis. The syntheses of lycoramine, galanthamine, yuehchukene analogues, ovalicin, studies toward the ingenol core, haemanthidine, pretazettine, tazettine, crinamine, Taxol, colombiasin A, elisapterosin B, the AB ring fragment of spongistatin 1 and 8-epipuupewhedione are discussed. Chapter 2: The convergent total synthesis of the marine natural product norrisolide is described. Both subunits, the hydrindane core and the norrisane side chain, are prepared in an asymmetric fashion through kinetic resolution and enantioselective cyclopropanation, respectively. A Shapiro reaction couples the two fragments and a Peterson olefination installs the 1,1-disubstituted olefin. Chapter 3: Preliminary experiments to isolate the biological target of norrisolide through reductive alkylation and tritium labeling are investigated. Further experiments are proposed to shed light on the primary norrisolide-protein interactions. / Thesis (PhD) — Boston College, 2009. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.