Development of New Catalytic Reactions for the Synthesis of Natural Products

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Chemical synthesis plays an important and often rate-limiting role in the fields of molecular medicine, agrochemicals, flavors and fragrances, and materials science. The development and application of new, selective, and efficient processes for the synthesis of functional molecules is therefore a fundamental area of research with broad societal impact. Dr. Sarah Reisman's research funded by this award is investigating new catalytic reactions as key carbon-carbon bond constructions for the synthesis of complex molecules with improved efficiency using the inexpensive and abundant metal, nickel. The research team is developing new reactions that couple different reaction partners as strategic steps in the synthesis of biologically active molecules. These investigations are providing more efficient and sustainable access to molecules with applications in medicine and agrochemicals. Dr. Reisman is engaged in outreach activities focused on improving curriculum for science, technology, engineering and mathematics (STEM) education in the Pasadena Unified School District, with a specific interest in encouraging young women to pursue STEM careers. With funding from the Chemical Synthesis Program of the Chemistry Division, Dr. Sarah Reisman at the California Institute of Technology is developing Ni-catalyzed cross-electrophile coupling (CEC) reactions as strategic reactions for natural product total synthesis. Advances in the synthesis of structurally complex, functional molecules are driven by the development of new synthetic methods to prepare carbon-carbon and carbon-heteroatom bonds, and the incorporation of these methods into increasingly sophisticated synthetic strategies. Dr. Reisman and her research team are developing new Ni-catalyzed double asymmetric reductive alkenylation reactions to prepare macrocycles, and Ni-catalyzed convergent fragment coupling reactions to prepare diterpenoid natural products. This research is contributing fundamental studies of Ni-catalyzed cross- electrophile coupling reactions, and demonstrating how Ni-catalyzed C(sp2)-C(sp3) bond constructions can be incorporated into synthetic strategy. In partnership with the Caltech Center for Teaching, Learning, and Outreach and the Community Science Academy, Dr. Reisman is developing organic chemistry experiments to enhance high school science curriculum in the Pasadena Unified School District (PUSD).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.