1. Practical synthesis of (−)-1-amino-1-deoxy-myo-inositol from achiral precursors
- Author
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Gonzalez-Bulnes, Patricia, Casas, Josefina, Delgado, Antonio, and Llebaria, Amadeu
- Subjects
- *
INOSITOL , *VITAMIN B complex , *ALCOHOLS (Chemical class) , *SUGARS - Abstract
Abstract: 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. [Copyright &y& Elsevier]
- Published
- 2007
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