Date of Award
Doctor of Philosophy
George A. Kraus
Organic synthesis is a highly-developed, useful, and interdisciplinary branch of natural science. Modern synthetic chemistry has provided complex molecules and new materials with unique properties. This study focused on creating new methodology, or new routes, to achieve a biologically active, natural product synthesis;A new methodology to generate 2,4-diacylfuran compounds has been developed and discussed. The synthesis of two natural 2,4-diacylfuran compounds, hibiscone C, and halenaquinone, has been achieved. The new route to hibiscone C features an efficient ring formation and rearrangement. Halenaquinone analogues have been synthesized by Michael addition, annulation, and palladium catalyzed reaction. The new route provides a new lead in the discovery of anticancer reagents like halenaquinone;A first approach towards building a BCD ring system for aquayamycin via intramolecular anion reaction is described. The approach could eventually provide a route to achieve the total synthesis of aquayamycin, a new antibiotic which might eventually be used to treat cancer.
Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/
Wan, Zhiwen, "Total synthesis of the natural furanones " (2000). Retrospective Theses and Dissertations. 13938.