Preparation of arylphosphonates of cyclic nucleotides

CHED 472

Amanda K. Meier, akmeier9407@webmail.winona.edu and Thomas W. Nalli, tnalli@winona.edu. Chemistry Department, Winona State University, Winona, MN 55987

Compounds similar to naturally occurring cyclic nucleotides, like cAMP and cTMP, could medicinally affect biological processes by way of specific phosphodiesterase inhibition.  Specifically this research attempted to synthesize a substituted phenylphosphonate analog of thymidine using Bentrude's methods for preparing thymidine cyclic methyl 3', 5'-phosphite (1) and reacting it with an iodonium salt.  

The iodonium salt reactions used a radical mechanism brought about by UV photolysis resulting in a phosphonate cyclic nucleotide (2).  The products were characterized utilizing 31P NMR and 1H NMR.