SmI2-mediated reactions of diethyl iodomethylphosphonate with esters and lactones:: a highly stereoselective synthesis of a precursor of the C-glycosyl analogue of thymidine 5′-(β-L-rhamnosyl) diphosphate

In the presence of samarium iodide diethyl iodomethylphosphonate reacts with esters to afford beta-ketophosphonates. The protocol has been applied to sugar lactones to afford in fairly good yields intermediates that are useful precursors for a variety of potentially bioactive compounds, such as the C-glycosyl analogue of thymidine 5'-(beta-L-rhamnosyl)diphosphate. (C) 2002 Elsevier Science Ltd. All rights reserved.