Photoredox-Catalyzed Deformylative 1,4-Addition of 2′-Deoxy-5′- O-phthalimidonucleosides for Synthesis of 5′-Carba Analogs of Nucleoside 5′-Phosphates

Article abstract of DOI:10.1021/acs.joc.8b00637

A concise approach for the synthesis of the 5′-carba analogs of nucleoside 5′-phosphates from 2′-deoxy-5′-O-phthalimidonucleosides by a visible-light-mediated deformylative 1,4-addition was developed. This method enabled rapid and facile generation of 4′-carbon radicals of nucleosides. Moreover, this synthetic strategy was applicable to the 5′-carba analogs of nucleoside 5′-phosphates as well as other 5′-carba nucleosides bearing methoxycarbonyl, cyano, and N-methylsulfamoyl groups.