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

Abstract

Abstract 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 &amp; Co. KGaA, 69451 Weinheim, Germany, 2003)