With the support of the Chemical Synthesis program in the Division of Chemistry, Professors Angus Lamar and Gordon Purser of the University of Tulsa are investigating new methods for the modification of arenols and heteroarenols, which are compounds commonly found in medicines, agricultural products, and advanced materials. The predictable decoration of an aromatic framework is a cornerstone of chemical synthesis, and significant effort has been devoted toward the expansion of a synthetic toolkit to allow for installation of molecular complexity. Despite the intense synthetic focus, access to certain substitution patterns of polysubstituted aromatics is largely restricted by intrinsic substituent effects. Due to this inherent activity, 1,2- and 1,4-substituent patterns dominate marketed drugs and chemical catalogs. The planned studies will provide direct architectural access to rarely observed polysubstituted bicyclic frameworks with 1,3-substituent patterns which will open the chemical landscape for the rapid construction of potentially bioactive frameworks that have thus far gone unexplored. During the funding period, the planned studies will provide Ph.D. students and undergraduate researchers with the opportunity to develop laboratory skills in chemical synthesis and computational chemistry, which will prepare them for careers in pharmaceutical, agrochemical, and materials industries. In addition, the researchers involved in this project will participate in STEM-related o