Novel class of difluorovinylphosphonate analogues of PEP

Abstract

A new class of difluorovinylphosphonate analogues of PEP, 4,4-difluoro-4-(diethoxyphosphinoyl)-2-methylenebutanoic acid 15, methyl 4,4-difluoro-4-(diethoxyphosphinoyl)-2-methylenebutanoate 17, (E)- and (Z)-4,4-difluoro-4-(diethoxyphosphinoyl)but-2-enoic acid 14 and 4,4-difluoro-4-phosphono-2-methylenebutanoic acid 16 have been synthesized. Methyl 3,3-difluoro-3-(diethoxyphosphinoyl)-2-hydroxy-2-methylpropionate 21 and the corresponding acid 3,3-difluoro-3-phosphono-2-hydroxy-2-methylpropionic acid 23, have also been synthesized. These compounds are designed to act as potential inhibitors in the shikimic acid pathway.