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

Podeschwa Michael | Zendy; Plettenburg Oliver | Zendy; vom Brocke Jochen | Zendy; Block Oliver | Zendy; Adelt Stephan | Zendy; Altenbach HansJosef | Zendy

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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)

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