Date of Award
Doctor of Philosophy
George A. Kraus
In this dissertation, we have investigated direct routes to several biologically important natural products.;Chapter 1 describes a concise construction of core skeleton of malibatol A, employing a novel benzofuran formation methodology and a regio- and stereoselective 7-membered ring formation via Lewis acid catalyzed epoxide ring opening as crucial steps.;Chapter 2 describes direct approaches to isoflavanquinones utilizing radical addition to quinones. Three main strategies were presented and were compared to generate radicals from the corresponding precursors.;Chapter 3 describes a direct entry to erogorgiaene, naturally occurring potent antitubercular agent, featuring a regioselective metal-halogen exchange and a 6-exo-trig radical cyclization as key transformations.;Chapter 4 describes synthetic studies towards antitubercular benzoxazole alkaloids. The core tricyclic skeleton of the originally proposed structures of these natural products was synthesized using an intermolecular Diels-Alder reaction as a key step.
Digital Repository @ Iowa State University, http://lib.dr.iastate.edu
Kim, Ikyon, "Direct approaches to natural product synthesis " (2003). Retrospective Theses and Dissertations. 918.