Cascade-based Syntheses of Four Complex Triterpenes

University Of Georgia Research Foundation Inc, Athens GA

Investigators

Abstract

Professor George Majetich in the Department of Chemistry at the University of Georgia is supported by the Organic and Macromolecular Chemistry Program for his research on the efficient syntheses of four triterpene natural products. The natural products will be synthesized from a common intermediate using a biomimetic cascade strategy to form three rings and several carbon-carbon bonds and asymmetric centers in one step. The stereochemistry of one of the triterpene natural products, peradione, has been previously determined by NMR analysis and is possibly incorrect. New insight into the correct stereochemistry of peradione will be achieved by the total synthesis of the preferred stereoisomer. With the support of the Organic and Macromolecular Chemistry Program, Professor George Majetich is developing new, more efficient ways to synthesize four structurally-related natural products. The synthetic pathways of these four organic compounds proceed through a common intermediate. In 1999 these natural products were isolated from a plant found in Central Asia which is used for treating liver disorders. There is a question as to whether the three-dimensional structure of one of these organic compounds has been correctly assigned. Professor Majetich's research should resolve this ambiguity.