Application of Acyl Aminals in Target and Function Oriented Synthesis

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This project will exploit the utility of acyclic N-acyl aminals in a range of important applications. N-Acyl aminals have been prepared through lengthy standard protocols but their availability from nitriles through a recently developed multicomponent reaction allows for access to greater structural diversity than has previously been available. This multicomponent reaction will be applied to the construction of a library of pederin analogs that would be difficult to access through previous approaches in an effort to minimize the toxicity of this potent immunosuppressive and cytotoxic agent. N-Acyl aminals will be used as precursors to N-acyliminium ions in studies that will validate the use of a capillary-based microreactor for rapidly screening the efficiency and mechanism of chiral acid catalyzed reactions. The capacity to design N-acyl aminals that cleave and release biologically active molecules through predictable stimuli will be utilized in the design of new drug delivery vehicles. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Paul Floreancig of the Department of Chemistry at the University of Pittsburgh. Professor Floreancig's research efforts revolve around the development and mechanistic analysis of new chemical reactions and the synthesis of biologically active molecules. This research will provide new opportunities for efficient syntheses of molecules that have tunable properties. Successful development of these projects will have an impact on lead generation and synthesis in the pharmaceutical and agricultural industries.