Preparation of Highly Substituted Cyclohexene Systems

University Of California-Los Angeles, Los Angeles CA

Investigators

Abstract

The focus of this research is the preparation of highly substituted cyclohexene systems using Lewis acid catalyzed Diels-Alder chemistry. Central to the research are two cycloaddition processes that allow the rapid and efficient preparation of very hindered cyclohexene systems in high yields with excellent diastereoselectivity. Since many natural products contain polysubstituted cyclohexane rings as an integral part of their structure, these methods allow for the construction of this class of compounds with a minimum number of steps. The new methodology will be applied to the synthesis of the cardiotonic agent ouabain, and N-methylwelwitindolinone C isothiocyanate, which reverses multiple-drug resistance (MDR). With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research and educational efforts of Dr. Michael E. Jung of the Department of Chemistry at the UCLA in Los Angeles. Professor Jung will focus his research on the development of new methods of chemical synthesis, and will apply these methods to natural products that have potential use in understanding heart disease, and in understanding why chemotherapy of cancer often fails. Graduate students and post-doctoral students will also be trained in Prof. Jung's laboratory.