Insertion of Arynes and Carbenes into a Diquinane Derivative for Natural Product Synthesis

With the support of the Chemical Synthesis (SYN) program in the Division of Chemistry, Professor Richmond Sarpong of the University of California–Berkeley will study methods for the insertion of reactive derivatives of benzene known as benzynes into five-membered organic compounds to prepare seven-membered rings. The methods that will be developed will streamline the preparation of complex organic molecules that have previously required more steps to prepare and introduce a completely new way to make families of compounds. The planned studies will provide a new platform for multi-step organic synthesis and train researchers in the science and art of chemical synthesis, which will prepare them for careers in the agrochemical, materials, and pharmaceutical industries. The goal of the proposed project is to develop the insertion of benzynes into 1,3-diketones, specifically in fused bicycles. The resulting ring-enlarged fused ring systems comprise the core of natural products in a wide range of natural products. Because the fused bicyclic substrates that will be employed are symmetrical, this project will also offer opportunities to develop enantioselective benzyne insertions for the first time. It is anticipated that this latter development will introduce a completely new way to prepare fused polycycles in enantioenriched form. This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.