Toward the Synthesis of Iejimalide B

This thesis discusses synthetic efforts made toward the total synthesis of the iejimalides (1 and 2a-d). The iejimalides exhibit potent cytotoxicity, however, they are only present in the biosphere in very low concentrations. Synthetic efforts are necessary to provide sufficient material for biological investigation. Two major subunits of the iejimalides have been synthesized: the R C1-C5 subunit and the N-formyl serine subunit. Efforts have also been made toward the synthesis of the revised C12-C20 subunit. These three key subunits are necessary to complete the total synthesis of the originally proposed and the revised structures of iejimalides B. One subunit, the N-formyl serine subunit, is also necessary for labeling studies of the iejimalides to determine the biological mode of activation.