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Stereoselective Synthesis of myo ‐, neo ‐, L ‐ chiro , D ‐ chiro , allo ‐, scyllo ‐, and epi ‐Inositol Systems via Conduritols Prepared from p ‐Benzoquinone
Author(s) -
Podeschwa Michael,
Plettenburg Oliver,
vom Brocke Jochen,
Block Oliver,
Adelt Stephan,
Altenbach HansJosef
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200200572
Subject(s) - chemistry , enantiomer , inositol , stereochemistry , stereoselectivity , total synthesis , cyclitol , resolution (logic) , biochemistry , receptor , catalysis , artificial intelligence , computer science
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)