Investigations of Macrocyles of Plant Origin

这一研究项目旨在制定合成植物来源的大环和具有不寻常特征的生物碱的战略，需要开发新的方法。一个特别令人关注的领域是氨基酸新的合成应用的开发；其他感兴趣的领域包括新的芳香醚合成和大环化方法。这些化学工作是在针对大环多肽Hymenocardine和astins C和D的全部合成工作的背景下进行的。进一步的研究将涉及合成氟化脯氨酸、Astin C的碳环类似物和顺氨键模拟物。有了这个奖项，有机和高分子化学计划支持宾夕法尼亚大学的Madeleine M.Joullie教授的研究。Joullie教授正在研究几种类似于小的循环蛋白质的分子的化学。这些自然产生的物质起源于植物界，尽管它们通常产生的量很少，而且它们在实验室中的制备相当具有挑战性。除了学习如何构建这种分子所涉及的科学好奇心之外，它们对它们的制药应用也很重要。例如，万古霉素家族的抗生素就属于这一类，而其他抗生素则显示出抗肿瘤活性。在实验室中对制造这些分子的方法进行彻底的研究将使评估它们的生物活性成为可能。

This research project is aimed at developing strategies for the synthesis of macrocycles of plant origin and alkaloids having unusual features requiring the development of new methodologies. An area of special concern is the development of new synthetic applications of amino acids; other areas of interest include new aryl-aryl ether syntheses and macrocyclization methodologies. These chemistries are being pursued in the context of total synthetic efforts directed toward the macrocyclic peptides hymenocardine and astins C and D. Further studies will involve the synthesis of fluorinated prolines, a carbocyclic analog of astin C, and a cis-amide bond mimic.With this Award, the Organic and Macromolecular Chemistry Program supports the research of Professor Madeleine M. Joullie of the University of Pennsylvania. Professor Joullie is studying the chemistry of several molecules that are akin to small, cyclic proteins. These naturally occuring substances originate in the plant kingdom although they are often produced in very small amounts, and their preparation in the laboratory is quite challenging. In addition to the scientific curiosity involved in learning how to build such molecules, they are important for their pharmaceutical applications. For example, the vancomycin family of antibiotics is included in this category, while others demonstrate antitumor activity. A thoroughgoing study of ways to make these molecules in the laboratory will make possible an evaluation of their biological activity.