Investigations of Macrocycles of Plant Origin

University Of Pennsylvania, Philadelphia PA

Investigators

Abstract

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.