| This thesis is separated into two parts: the synthesis of the marinomycins and their monomeric counterparts, and the studies toward the total synthesis of the lomaiviticins. Background on antibiotic resistance, the isolation of the marinomycins by the Fenical lab, and our retrosynthetic analysis of the marinomycins is included in Chapter 1. In Chapter 2, our synthesis of the marinomycin monomeric counterparts, our attempted dimerizations to form the marinomycins, and our step-wise synthesis of the marinomycins is included. Chapter 3 focuses on the background of the lomaiviticins, including the isolation and structure determination of the kinamycins (a related family of natural products) and the lomaiviticins, approaches by other groups to the diazoparaquinone natural products, our original approach to the lomaiviticins (early-stage dimerization), and our modified approach to the lomaiviticins (late-stage dimerization). We then go on to synthesize the kinamycins (Chapter 4) as an elaborate model system of the lomaiviticin monomer, and use our acquired knowledge this approach to synthesize the lomaiviticin aglycon monomer, and explore a late-stage dimerization of this monomer (Chapter 5). |
