This project addresses the development of catalytic methods for the formation of carbon-nitrogen and carbon-carbon bonds. Stereocontrolled arylation of vinylic carbons and the development of new ligands for nucleoside modification and other applications will be examined. Solution chemistry will be translated to polymer-supported analogs using a traceless linker approach for high-throughput, diversity-oriented studies. Palladium catalyzed methods for embedding novel biologically important natural product structures into nucleoside cores will also be examined. Complementary catalysis by Pd and Cu or Pd and Ru, in which one specific catalyst can be used to achieve C-C reactions whereas another can be used for C-N bond formation within a single substrate, will provide new structural motifs and offer stereocontrol that cannot be otherwise attained.
With the support of this award from the Organic and Macromolecular Chemistry Program, Professor Mahesh K. Lakshman, of the Department of Chemistry at CUNY City College, is developing new catalytic reactions applicable to the controlled and efficient synthesis of modified nucleosides. Modified nucleosides are of high importance and value, with a broad range of applications spanning from new pharmacological agents against emerging diseases as well as existing ones, probes of biomolecular function and new paradigms within the context of molecular self-assembly. These reactions will be effected using palladium catalysis, a powerful organic synthesis methodology. The confluence of palladium-catalyzed reactions and nucleoside chemistry is expected to lead to new and unusual structural motifs with wide ranging potential applications.
