Facile syntheses of all possible diastereomers of conduritol and various derivatives of inositol stereoisomers in high enantiopurity from myo-inositol.
Phosphoinositide-based signaling processes are crucially important in intracellular signal transduction events. Inositol phosphate analogues have been useful in probing the structure-activity relationships between inositol phosphates and biomacromolecules, and in studying biological functions of newly found inositol phosphates. Thus, a systematic and ready access to inositol stereoisomers is highly desirable. And practical and convenient syntheses of conduritols and related compounds are also important because of their biological activities and their synthetic utilities in the preparation of other bioactive molecules. We herein report the first syntheses of all possible diastereomers of conduritol and various derivatives of eight inositol stereoisomers in high enantiopurity from myo-inositol, which involve efficient enzymatic resolution of the intermediates conduritol B and C derivatives, followed by oxidation-reduction or the Mitsunobu reaction, and cis-dihydroxylation in stereo- and regioselective manners.
Kwon
Yong-Uk
YU
Department of Chemistry, Division of Molecular and Life Sciences, Pohang University of Science & Technology, Pohang 790-784, South Korea.
Lee
Changgook
C
Chung
Sung-Kee
SK
D002175:Candida / Q000201:enzymology; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D002855:Chromatography, Thin Layer; D003511:Cyclohexanols / Q000138:chemical synthesis* / Q000378:metabolism; D053138:Cyclohexenes; D006900:Hydroxylation; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D008049:Lipase / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D020103:Rhizomucor / Q000201:enzymology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D003511:Cyclohexanols; D053138:Cyclohexenes; C090988:conduritol B; D007294:Inositol; D008049:Lipase