Paul Floreancig

Organic Synthesis

Our research is directed toward developing fundamentally new transformations and highlighting their utility for complex molecule synthesis. Much of our work in reaction design has been devoted to utilizing oxidation processes to form electrophiles. These processes exploit the high but predictable cleavage patterns of radical cations and utilize unconventional leaving groups such as benzyl radicals of hydrogen atoms as leaving groups in cation-forming reactions. These studies draw heavily upon basic principles of physical organic chemistry to provide highly chemoselective and efficient cyclization reactions that proceed under mild conditions.

We are also devising methods that utilize the capacity of nitriles to act as precursors to highly functionalized amides. This multicomponent process proceeds through nitrile hydrozirconation, acylation of the resulting metalloimine, and nucleophilic addition to the intermediate acylimine. The process can be applied to the formation of carbon–carbon or carbon–heteroatom bonds, making it quite useful for applications to combinatorial and diversity-oriented synthesis. The generally inert nature of nitriles also creates unique strategic opportunities for target-oriented synthesis that minimize protecting group manipulations.

The inspiration for our efforts in natural product synthesis range from preparing inaccessible materials with interesting biological activities to demonstrating the capacity of our methods to function in a complex setting. Examples of complex structures that we have recently prepared are shown below.