Synthesis of oseltamivir containing phosphonate congeners with anti-influenza activity

摘要

Novel phosphonate compounds are described. The compounds have activity as neuraminidaseinhibitors against wild-type and H274Y mutant of H1N1 and H5N1 viruses. The presentdisclosure also provides an enantioselective synthetic route to known neuraminidaseinhibitors oseltamivir and the anti-flu drug Tamiflu®, as well as novelphosphonate compounds, via D-xylose. Another efficient and flexible synthesisof Tamiflu and the highly potent neuraminidase inhibitor Tamiphosphor was alsoachieved in 11 steps and 20% overall yields from the readily available fermentationproduct (1