Flexible stereo- and regioselective synthesis of myo-inositol phosphates (Part 1):: Via symmetrical conduritol B derivatives

A practical route is described for the preparation of myo-inositol polyphosphates. Optically pure myo-mositol derivatives can be prepared from p-benzoquinone in both forms by enzymatic resolution of a C-2-symmetric diacetoxyconduritol B key intermediate, followed by cis-dihydroxylation. Selective functionalization of axial and equatorial hydroxy groups allows the synthesis of symmetric mositol phosphates as well as unsymmetrical, enantiomerically pure mositol phosphates. (c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.