Research in Jon’s Group is focused on two main areas of investigation. One part of the group is dedicated to the development of useful new synthetic reactions, while the other half is committed to designing and executing creative efficient routes towards natural products with promising biological profiles. Exciting outgrowths of these two programs are the unique structural product collections they afford. In our world, these valuable collections then find a new home in the assays of our biological collaborators and begin their new journey filled with exciting unknown observations and discoveries. Currently, we are working on advancing three main methodological programs: These programs are dedicated to designing and studying: 1) new catalytic ring expansion of strained heterocyclic structures, 2) valuable reaction cascades and 3) new reagents for oxidative dearomatizations. Students working on these important programs are expected to demonstrate to the community the full scope and limitations of their new discovery, and investigate mechanism and develop asymmetric variants of the reaction when appropriate. I view a well-matched application of their new reaction towards a natural product, pharmaceutical agent or other valuable target structures to be an important part of their training. Our natural product portofolio is primarily dedicated to the synthesis of complex bridged bicyclic structures. Each target structure is carefully selected for its unique architecture and reported biological activity. Students are expected to devise synthetic blueprints that are both creative and concise. Each synthetic path should be based on a novel disconnection approach that should also employ a new or underutilized reactions or reaction sequences. It is expected that many of these approaches will serve as examples or inspirations for others to follow in their molecular designs. Targets of interest in this category include vinigrol, hypoestoxide, hyperforin, verticillol and guttiferone G. Following completion these targets otherwise inaccessible natural product hybrid collections will be assembled and tested in appropriate assays in addition to being screened further for alternate functional value or insights.