Practical synthesis of all inositol stereoisomers from myo-inositol.
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.
Chung
S K
SK
Department of Chemistry, Pohang University of Science & Technology, Korea.
Kwon
Y U
YU
D006900:Hydroxylation; D007294:Inositol / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
D007294:Inositol