Stereoselective Synthesis of myo‐, neo‐, L‐chiro, D‐chiro, allo‐, scyllo‐, and epi‐Inositol Systems via Conduritols Prepared from p‐Benzoquinone

A practical route is described for the flexible preparation of a wide variety of inositol stereoisomers and their polyphosphates. The potential of this approach is demonstrated by the synthesis of myo ‐, L ‐ chiro ‐, D ‐ chiro ‐, epi ‐, scyllo ‐, allo ‐, and neo ‐inositol systems. Optically pure compounds in either enantiomeric form can be prepared from p ‐benzoquinone via enzymatic resolution of a derived conduritol B key intermediate. High‐performance anion‐exchange chromatography with pulsed amperometric detection permits inositol stereoisomers to be resolved and detected with high sensitivity. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)