American Chemical Society
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Stereocontrolled Transformation of Nitrohexofuranoses into Cyclopentylamines via 2-Oxabicyclo[2.2.1]heptanes:  Incorporation of Polyhydroxylated Carbocyclic β-Amino Acids into Peptides

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journal contribution
posted on 2003-03-29, 00:00 authored by Raquel G. Soengas, Juan C. Estévez, Ramón J. Estévez
A promising new strategy for the transformation of nitrohexofuranoses into cyclopentylamines, based on intramolecular cyclization followed by controlled opening of the resulting 2-oxabicyclo[2.2.1]heptane derivatives, allowed the first total synthesis of a carbocyclic β-amino acid and its incorporation into peptides. This strategy also afforded a new route to cyclopentylamines with well-known glycosidase inhibition properties.