New Methods for Natural Product Synthesis

Syracuse University, Syracuse NY

Investigators

Abstract

Professor Nancy I. Totah of Syracuse University is supported by the Chemical Synthesis Program of the Chemistry Division to develop new methods for the efficient preparation of compounds that contain functionalized tetrahydropyrans and their derivatives. This research is focused on the use of exocyclic enol ethers for the formation of carbon-carbon bonds. Specifically, this research is directed towards the use of 2-methylenetetrahydropyrans in carbonyl ene and related processes. In addition, it explores the direct addition, tandem, and two-directional manifestations of this process and the development of efficient, enantioselective protocols. Carbon-carbon bond forming reactions that capitalize on the nucleophilic nature of exocyclic enol ethers have been underutilized. These studies will provide fundamental knowledge about the chemistry of 2-methylenetetrahydropyrans, and will provide a basis for the further manipulation of these interesting substrates in complex molecule synthesis. Tetrahydropyrans and their derivatives are common components of molecules that have useful biological activity and interesting structural features. The exploration, development, and application of the chemistry proposed in this application will provide new methods and strategies for the introduction and manipulation of tetrahydropyrans. Such efforts benefit society at large by providing improved access to molecules with important applications in medicine, agriculture, and materials chemistry. Further, this project will provide training for graduate students, postdoctoral associates and undergraduates, including those from groups historically underrepresented in the sciences.