Investigations of Macrocycles of Plant Origin

本研究的重点是开发制备大环的合成路线。将寻求形成[9]和[10]对环番的方法以及大环化和大内酰胺化的方法。对于大内酰胺，将使用氨基与硫代酯在银盐存在下的反应，并将研究一种利用叠氮化物作为潜在官能团的方法。将进行膜卡因、丽春藤和罗奎福汀C的全合成，以突出战略方法。有了这个更新的奖项，有机和高分子化学计划将支持宾夕法尼亚大学化学系的Madeleine M.Joullie博士的研究。Joullie教授将专注于开发合成不寻常类天然产物的策略，包括植物来源的大环和具有不寻常结构特征的生物碱。从植物或其他自然来源获得的这些化合物的产率很低，因此开发实用的合成方法非常重要。目标分子的生物学特性是制药业感兴趣的。这项研究也为研究生和博士后的培养提供了良好的环境。

The focus of this research is the development of synthetic routes for the preparation of macrocycles. Methods to form [9] and [10]paracyclophanes and approaches to macrocyclization and macrolactamization will be pursued. For macrolactamization, the reaction of amino groups with thioesters in the presence of silver salts will be used and an approach utilizing an azide as latent funcionality will be investigated. The total syntheses of hymenocardine, pondaplin and roquefortine C will be carried out to highlight the strategic approach.With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Madeleine M. Joullie of the Department of Chemistry at the University of Pennsylvania. Professor Joullie will focus her work on developing strategies for the synthesis of unusual classes of natural products including macrocycles of plant origin and alkaloids exhibiting unusual structural features. The low yields of these compounds obtained from plants or other natural sources make the development of practical synthetic methods important. The biological properties of the target molecules are of interest to the pharmaceutical industry. The research also provides an excellent setting for the training of graduate and post-doctoral students.