Bioorganic & medicinal chemistry letters

Practical synthesis of all inositol stereoisomers from myo-inositol

SK Chung, YU Kwon

Index: Chung, Sung-Kee; Kwon, Yong-Uk Bioorganic and Medicinal Chemistry Letters, 1999 ,  vol. 9,  # 15  p. 2135 - 2140

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Citation Number: 27

Abstract

Synthesis of six inositol stereoisomers was successfully carried out via conduritol intermediates prepared from myo-inositol. Dihydroxylation and epoxidation followed by ring opening of the conduritol B, C and F derivatives gave epi-, allo-, muco-, neo-, dl-chiro-and scyllo-inositol. The cis-inositol derivative, which may not be prepared by this approach, was synthesized in 5 steps via 2-O-benzoyl-myo-inositol orthoformate as the key intermediate.