Convenient synthesis of 3- and 6-deoxy-d-myo-inositol phosphate analogues from (+)-epi- and (−)-vibo-quercitols

Starting from (+)-epi- and (−)-vibo-quercitols readily produced by bioconversion of myo-inositol, some biologically interesting phosphate and polyphosphate analogues, including the Ins(1,4,5)P3 derivatives of 3-deoxy- and 6-deoxy-d-myo-inositol, could be readily prepared in a conventional manner. In addition, chemical modification at C-2 of the 3-deoxy Ins(1,4,5)P3 provided 2-epimer, and 2-deoxy and 2-deoxy-2-fluoro forms. Eight polyphosphate analogues obtained were assayed for biological activity against PDH-Pase and PDH-K, and G6Pase, but none proved positive.