A synthetic route from D-glucose to D-myo-inositol-1,4,5- tris(dihydrogenphosphate): Use of an unusual ene reaction and the Bu2SnCl2/Bu2SnH2 reagent

Article abstract of DOI:10.1016/S0040-4039(98)00792-8

D-Glucose was converted into the propargylsilane aldehyde 3, which underwent ring closure with retention of silicon, in the presence of camphorsulfonic acid, to give 5, and this was elaborated, via ketone 22, into 2, which had previously been transformed into D-myo-inositol-1,4,5- tris(dihydrogenphosphate). A crucial step in the synthesis is the stereoselective reduction of 22 with Bu₂SnCl₂/Bu₂SnH₂, a reagent system that shows a strong preference for generating equatorial alcohols.