Practical synthesis of all inositol stereoisomers from myo-inositol

• Published in: Bioorganic & medicinal chemistry letters 1999-08, Vol.9 (15), p.2135-2140
• Main Authors: Chung, Sung-Kee, Kwon, Yong-Uk
• Format: Article
• Language: English
• Subjects: Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemistry; Exact sciences and technology; Hydroxylation; Inositol - analogs & derivatives; Inositol - chemical synthesis; Inositol - chemistry; Organic chemistry; Preparations and properties; Stereoisomerism
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(99)00348-0

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. 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.