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

6 pages, 3 schemes.-- PMID: 17524374 [PubMed].-- Printed version published on Sep 3, 2007.A new synthesis of enantiomerically pure 1-amino-1-deoxy-myo-inositol is reported. The route described employs pbenzoquinone, 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.Financial support from Ministerio de Educación y Ciencia (Spain) (CTQ2005-00175/BQU), Ministerio de Sanidad y Consumo (FIS PI040767), and Fondos Feder (EU), DURSI (Generalitat de Catalunya: Project 2005SGR01063) is acknowledged. P.G.B. thanks Ministerio de Educación y Cultura (Spain) for a predoctoral fellowship.Peer reviewe