Dearomatization Reactions in Synthesis

With this Award, the Chemical Synthesis Program of the NSF Division of Chemistry is supporting the research of Professor Christopher M. Beaudry of Oregon State University who is investigating new chemical reactions that are used to prepare pharmaceuticals, fine chemicals, and building-block molecules for the chemical industry. Aromatic rings are common features of many fine chemicals. Traditionally, aromatic rings are viewed as stable, less reactive chemical entities; however, the Beaudry group is developing new reactions to harness their underutilized reactivity. They will enable more efficient syntheses of clinical pharmaceuticals such as homoharringtonine (for leukemia), ergometrine (for postpartum bleeding), and novel lead compounds such as himgaline (potential applications in cardiovascular research). Educational benefits of this research include training PhD students and undergraduates for careers in the chemical industry. Additionally, outreach activities in Oregon schools involve the Corvallis public school system. Professor Beaudry and his research team develop new pericyclic reactions of aromatic rings that transform these molecules into new value-added molecules. Specifically, they are transforming benzenes, pyrones, pyridines, and related starting materials into other cyclic and polycyclic products with control over substitution. The research leverages the contiguous unsaturated carbons of the arene starting materials to give densely functionalized products. A key aspect is the recognition that polarized cycloaddition coupling partners offer increased reactivity and regioselectivity in these bond constructions. This work solves long-standing problems in chemical synthesis, such as the preparation of 4-substituted indoles, 2,3-disubstituted phenols, and nitrogen-containing bicyclic systems. Broader impacts of the work include training chemists in the practice and strategy of sophisticated organic synthesis; preparation that serves them well for careers in the agrochemical, pharmaceutical, and fine chemical industries. Longer term benefits of this research may obtain as the development of step-saving, convergent syntheses of high value-added targets could lead to more efficient processes for the manufacture of these targets. Moreover, the Beaudry group is actively engaged in reaching under-represented minorities and first-generation college students and in providing them with exposure to modern research in synthetic chemistry. 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.