Practical synthesis of all inositol stereoisomers from myo-inositol

Citation
Sk. Chung et Yu. Kwon, Practical synthesis of all inositol stereoisomers from myo-inositol, BIOORG MED, 9(15), 1999, pp. 2135-2140
Citations number
58
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
9
Issue
15
Year of publication
1999
Pages
2135 - 2140
Database
ISI
SICI code
0960-894X(19990802)9:15<2135:PSOAIS>2.0.ZU;2-C
Abstract
Synthesis of six inositol stereoisomers was successfully carried out via co nduritol intermediates prepared from myo-inositol. Dihydroxylation and epox idation followed by ring opening of the conduritol B, C and F derivatives g ave epi-, allo-, muco-, neo-, DL-chiro- and scyllo-inositol. The cis-inosit ol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediat e. (C) 1999 Elsevier Science Ltd. All rights reserved.