New Cycloaddition and Annulation Strategies for Organic Synthesis

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In this project supported by the Chemical Synthesis Program of the Chemistry Division, Professor Rick L. Danheiser of the Department of Chemistry at the Massachusetts Institute of Technology will develop new methods for the "annulation-based" synthesis of cyclic organic molecules. Carbocyclic and heterocyclic ring systems are often found in the structures of biologically important compounds, including those with applications in medicine and agriculture. Such compounds also are of interest for materials chemistry or electronics applications. Therefore, the development of new methods for their synthesis that are both streamlined and complementary to more traditional methods, is of broad scientific interest. The synthetic methods developed in the proposed research will provide researchers in both academia and industry with new tools for the synthesis of such important heterocyclic compounds. The graduate students supported under this program will receive training to develop their skills as synthetic chemists, and to develop their oral and written communication skills. The graduate students will also serve as coordinators for the MIT Outreach Program to high schools in the New England region an important component of which is directed at reaching out to members of groups traditionallys underrepresented in the STEM disciplines.Synthesis is often described as the "enabling technology" of chemistry. Pericyclic reactions serve as the primary vehicle to be exploited in this research, with most efforts focused on the design of convergent benzannulation strategies based on cascades of pericyclic reactions. A key feature of the proposed research is the development of new synthetic reactions based on the chemistry of strained and unusual molecules as building blocks. The new methods will be applied to provide rapid access to highly substituted heterocyclic systems including indoles and pyridines.