In this project funded by the Chemical Synthesis program of the Chemistry Division, Professor Rich Carter of Oregon State University is developing proline sulfonamide-catalyzed methods for the synthesis of stereochemically rich building blocks and applying these in natural product synthesis. Proline sulfonamide-based catalysts enable chemists to avoid the use of toxic metals to access important chemical building blocks. Co-principal investigator Paul Ha-Yeon Cheong is exploring the mechanistic underpinnings of these reactions computationally. Natural products being synthesized through this award expand the chemical strategies available to the scientific community and lead to efficiency gains in the construction of terpenes. An impact of this research includes the founding of a company, based in part on this work, which provides opportunities for student training. The research provides a unique training environment for students through a highly collaborative research program that integrates organic synthesis and computations.
This project focuses on the development of novel organocatalytic reaction pathways to access disubstituted cyclohexenones. The widespread presence of stereogenic quaternary centers in natural products has made their construction a central focus of organic chemistry; however, practical methods continue to be critically needed. The development of this chemistry features a close relationship between computation and experiment that reduces reaction time development. Methodologies developed and studied in this proposal will be utilized in synthesizing the natural products obtusanal A and wortmannin.
