Practical synthesis of (-)-1-amino-1-deoxy-myo-inositol from achiral precursors

Carbohydr Res. 2007 Sep 3;342(12-13):1947-52. doi: 10.1016/j.carres.2007.04.024. Epub 2007 May 5.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Indicators and Reagents
  • Inositol / analogs & derivatives*
  • Inositol / chemical synthesis
  • Inositol / chemistry
  • Models, Molecular
  • Molecular Conformation

Substances

  • Indicators and Reagents
  • Inositol
  • myo-inosamine