Successful cascade-based processes require a rigorous understanding of the scope and limitations of the starting compounds, every reagent used, every conceivable reaction intermediate generated during the course of the reaction, and the compatibilities of all of these variables throughout each set of conditions employed in the course of a given transformation. The focus of this project is the efficient asymmetric synthesis of four complex triterpenes - salvadiol, salvadiones A and B, and "peradione" - in which several rings and virtually all of the asymmetric centers are created in biomimetic fashion from a common intermediate.
With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. George Majetich of the Department of Chemistry at the University of Georgia. A dominant goal in synthetic organic chemistry is the design of efficient and stereoselective synthetic strategies. One way of devising the most efficient synthetic route possible for a given compound is to recognize when two or more transformations can be achieved at the same time under the same reaction conditions, without isolation of the intermediate products. Indeed, the greater number of sequential transformations that can occur, the fewer the steps needed to achieve a given total synthesis and the more efficient the synthesis. This is the driving force and intellectual merit of "cascade"-based processes in organic synthesis. The synthesis of the four complex triterpenes by Professor Majetich and his students will enhance our knowledge of cascade reactions and further the development of new and efficient ways to prepare biologically interesting compounds. These factors are of tremendous importance for the practice of organic synthesis both for academic research and for industrial applications.
