Stereoselective Synthesis of myo-, neo-, L-chiro, D-chiro, allo-, scyllo-, and epi-Inositol Systems via Conduritols Prepared from p-Benzoquinone
✍ Scribed by Michael Podeschwa; Oliver Plettenburg; Jochen vom Brocke; Oliver Block; Stephan Adelt; Hans-Josef Altenbach
- Publisher
- John Wiley and Sons
- Year
- 2003
- Tongue
- English
- Weight
- 280 KB
- Volume
- 2003
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
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 & Co. KGaA, 69451 Weinheim, Germany, 2003)