Practical synthesis of (-)-1-amino-1-deoxy-myo-inositol from achiral precursors.
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.
Gonzalez-Bulnes
Patricia
P
Research Unit on Bioactive Molecules (RUBAM), Departament de Química Orgànica Biològica, Institut d' Investigacions Químiques, i Ambientals de Barcelona (IIQAB-CSIC), Jordi Girona 18-26, 08034 Barcelona, Spain.
Casas
Josefina
J
Delgado
Antonio
A
Llebaria
Amadeu
A
D007202:Indicators and Reagents; D007294:Inositol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation
D007202:Indicators and Reagents; D007294:Inositol; C008572:myo-inosamine