Photoelectrocyclizations to Anti-Inflammatory Natural Products

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With the support of the Chemical Synthesis (SYN) program in the Division of Chemistry, this University of Utah team (Dr. Andrew Roberts serves as substitute-PI for Jon Rainier) will study the generation and structural elaboration of small molecule anti-inflammatory agents. The means with which the Rainier team intends to generate the anti-inflammatories will involve electrocyclization reactions. Toward these goals, Rainier and his coworkers will work to develop, optimize, and utilize chemistry that promises to convert readily available precursors into relatively complex molecular systems using environmentally sustainable reagents, namely light. In addition to the science being developed, this award also promises to help to develop the next generation of scientists who will, following their graduation, go on to careers in industry and academia helping to develop new chemistry and important medicines, materials, agricultural products, and chemicals.The photoelectrocyclization studies outlined in this award provide for a creative route into the scaffolds of important anti-inflammatory agents. The core model systems to be explored are bis- and mono-arylcyclobutenones from cross-coupling reactions, converting these into relatively complex polycyclic systems. The Rainier group intends to examine the effect of substrate, substitution, reaction conditions, and additives on the electrocyclization reactions of bis-aryl alkenes. These efforts will be focused on studying the efficiency of each reaction and the dependency of the observed stereochemical outcomes on each of the variables. More fundamentally, these studies are expected to provide an enhanced understanding of excited state reactivity and will test the ability to trap and manipulate reactive intermediates generated through such photoelectrocyclization reaction manifolds.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.