Sonogashira coupling in the synthesis of modified 2'-deoxyribonucleoside derivatives

ORGN 158

Felix N Ngassa, ngassaf@gvsu.edu and Matthew T. Van Gessel, ngassaf@gvsu.edu. Department of Chemistry, Grand Valley State University, 1 Campus Drive, Allendale, MI 49401
Modified purine nucleoside derivatives have attracted wide pharmaceutical interest as a result of the vast array of biological functions of these molecules. The application of Sonogashira coupling is well documented for the synthesis of ribonucleoside derivatives, but the application of this coupling method to the synthesis of the more labile 2'-deoxy nucleoside analogs is ongoing. A systematic approach involving optimization of reaction conditions for effective coupling was the focus of this project. The effect of changing base, solvent, reaction temperature, catalyst, and substrate were investigated. The implications of the results were evaluated in terms of the impact on the synthetic versatility of the Sonogashira coupling in modified 2'deoxyribonucleosides. Results of the optimization studies will be presented.