Date of Award
Doctor of Philosophy
George A. Kraus
In this dissertation, we have investigated the direct and efficient synthetic route to biologically active natural products;Chapter 1 describes a concise and efficient synthetic route to the highly funtionalized tricyclic core skeleton of papuaforin B. In the course of the synthesis, an efficient cyclization method using Na/NH3 was demonstrated. Newly developed bromination method leading to an alpha-bromoenone would serve as a handle for construction of the fused pyran ring of papuaforin B. Further efforts along this line are in progress;Chapter 2 describes the direct synthesis of 7,8-dihydroxycalamenene, which includes the successful application of allylic strain in the stereoselective synthesis. Interestingly, Mansonone C, a potent antifungal agent, was also obtained as the co-product from the same starting material. Application of this synthetic strategy to the synthesis of analog natural products is in progress.
Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/
Jeon, Insik, "New synthetic methods for hypericum natural products " (2006). Retrospective Theses and Dissertations. 1874.