Design and Application of New Pericyclic Strategies

The overarching theme of our research program concerns the development of new and general pericyclic strategies that enable efficient access to complex cyclic frameworks of biological importance. A hallmark of our approach is the design of atypical cycloaddition reaction partners that are at a high oxidation level (i.e., large degree of heteroatom incorporation and/or unsaturation) in order to confer unique reactivity, while also minimizing the need for redox manipulations post cycloaddition. A significant challenge within this area is the development of methods that remain operationally friendly, for highly unsaturated heteroatom-rich molecules often exhibit challenging stability profiles. Generally speaking, our approaches leverage fundamental structure and reactivity studies to inform the optimization of our proposed reaction partners in order to gain kinetic stability without sacrificing desired reactivity. Once we have developed a new methodology, our focus pivots toward applications in target-oriented synthesis, typically merging our abiotic pericyclic methodologies with bioinspired cascades.