Preparation of Highly Substituted Cyclohexene Systems

本研究的重点是利用Lewis酸催化的Diels-Alder化学制备高取代环己烯体系。这项研究的中心是两个环加成过程，这两个过程允许快速有效地制备非常受阻的环己烯体系，产率高，非对映选择性好。由于许多天然产物含有多取代环己烷环作为其结构的组成部分，这些方法允许以最少的步骤构建这类化合物。新方法将用于合成强心剂哇巴因和逆转多药耐药性(MDR)的N-甲基韦林酮C异硫氰酸酯。通过这个续展奖项，有机和高分子化学项目支持洛杉矶加州大学洛杉矶分校化学系的Michael E.Jung博士的研究和教育努力。荣格教授将把他的研究重点放在开发新的化学合成方法上，并将这些方法应用于天然产品，这些产品可能会在理解心脏病和了解癌症化疗经常失败的原因方面发挥作用。研究生和博士后也将在Jung教授的实验室接受培训。

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.