Regioselective phosphorylation of -inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol

A regioselective phosphorylation method for myo -inositol was developed by utilizing readily preparable BINOL-derived phosphoramidites. The method also facilitated the complete separation of the diastereomeric products by simple chromatography. Based on this phosphorylation and Ni-catalyzed alkyl-alkyl cross-coupling reaction for long fatty acids, we achieved the first synthesis of a lysophosphatidylinositol, EhPIa having long fatty acid C30:1, as a partial structure of glycosylphosphatidylinositol (GPI) anchor from the cell membrane of a protozoa, Entamoeba histolytica . BINOL-derived phosphoramidites enabled a regioselective phosphorylation of myo -inositol. The method was applied for the first total synthesis of a protozoan lysophosphatidylinositol, EhPIa.