Investigations of Macrocyles of Plant Origin

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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.