Two areas that continue to fascinate the chemistry community are the total synthesis of complex natural products and the application of combinatorial chemistry to natural products and natural product-like molecules. This thesis outlines recent studies in both of these frontiers in chemistry. First, the daunting chemical architecture of azadirachtin has flummoxed synthetic chemists for over two decades. A recent effort was undertaken by our laboratory to create novel solutions to the overarching problem in the synthesis of azadirachtin, namely the formation of the C 8 -C14 bond. Chapter two describes our initial explorations toward C8 -C14 bond formation via organometallic chemistry. Chapter three details an enantioselective entry into the azadirachtin framework through radical chemistry and cascade reactions. This route remains our central focus in the drive toward the total synthesis of azadirachtin. Second, chapter four details a study in the application of natural product-like libraries to chemical biology. Specifically, we utilized a novel library based on a 2,2-dimethylbenzopyran scaffold to discover potent and selective agonists for the farnesoid X receptor (FXR). Finally, chapter five outlines an exploration in the technology development of privileged templates on solid support, namely indolines and indoles. Using a novel phenylselenenyl bromide resin, we were able to develop several novel solid phase syntheses of 2-methyl indolines, polycyclic indolines, 2-methyl indoles, and 2-propenyl indolines.
Rialto, California has always been a growing place. At first a charming town populated mostly by citrus growers, the city seemed to know no limits in the 1950s as Route 66 attracted more and more commuters to the area. For several years, Rialto was officially the fastest-growing city in the United States. Rialto's lush groves and towering eucalyptus windbreaks were gradually replaced by subdivisions, but the spectacular San Gabriel and San Bernardino Mountains remained.
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