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Title

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

AuthorsGonzález-Bulnes, Patricia ; Casas Brugulat, Josefina; Delgado Cirilo, Antonio ; Llebaria, Amadeu
KeywordsAminoinositol
Conduritol B
Myo-Inositol
Aminoconduritol
Enantiomer
Kinetic resolution
Issue Date5-May-2007
PublisherElsevier
CitationCarbohidrate Research 342(12-13): 1947-1952 (2007)
AbstractA 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.
Description6 pages, 3 schemes.-- PMID: 17524374 [PubMed].-- Printed version published on Sep 3, 2007.
Publisher version (URL)http://dx.doi.org/10.1016/j.carres.2007.04.024
URIhttp://hdl.handle.net/10261/9509
DOI10.1016/j.carres.2007.04.024
ISSN0008-6215
Appears in Collections:(IQAC) Artículos
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