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A new synthesis of enantiomerically pure 1-amino-1-deoxy-myo-inositol is reported. The route described employs p-benzoquinone, an achiral compound, as the starting material to give conduritol B tetraacetate in three steps. Kinetic resolution of this compound using a palladium catalyst with a chiral ligand allows access to a conduritol B tetraester in high enantiomeric excess. This compound is transformed into tetrabenzyl conduritol B epoxide, which is regioselectively opened with azide to give the key azidocyclitol. Final transformation into (-)-1-amino-1-deoxy-myo-inositol hydrochloride is achieved in four synthetic steps. This sequence allows the synthesis of this compound in high enantiomeric purity in a semi-preparative scale.
Models, Molecular, Aminoinositol, Enantiomer, Conduritol B, Kinetic resolution, Molecular Conformation, Myo-Inositol, Indicators and Reagents, Inositol, Aminoconduritol
Models, Molecular, Aminoinositol, Enantiomer, Conduritol B, Kinetic resolution, Molecular Conformation, Myo-Inositol, Indicators and Reagents, Inositol, Aminoconduritol
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