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Efficient synthesis of 2,6,7,8-tetrahydroxyindolizidines (castanospermine analogues) via the dipolar cycloadditions of N-benzyl-C-(tetrofuranos-4-yl)nitrones to methyl acrylate

AuthorsTorres-Sánchez, Mª Isabel; Borrachero, Pastora; Cabrera-Escribano, Francisca; Gómez-Guillén, Manuel; Angulo-Álvarez, Manuel; Álvarez, Eleuterio ; Favre, Sylvain; Vogel, Pierre
Methyl acrylate
Dipolar cycloaddition
Glycosidase inhibitors
Issue Date4-Sep-2007
CitationTetrahedron Asymmetry 18(15): 1809-1827 (2007)
AbstractThe dipolar cycloaddition of (Z)-N-benzyl-(3-O-benzyl-1,2-O-isopropylidene-α-d-ribofuranos-5-ylidene)amine N-oxide to methyl acrylate gives a 53:16:26:5 diastereomeric mixture of isoxazolidine derivatives. The dipolar cycloaddition of the xylo analogue to methyl acrylate is more diastereoselective, producing a 44:13:43 mixture of only three diastereomers. The ribo-configured adducts have been converted (4 steps only) into the new (2R,6S,7S,8R,8aR)-, (2S,6S,7S,8R,8aR)-, (2S,6S,7S,8R,8aS)- and (2R,6S,7S,8R,8aS)-2,6,7,8-tetrahydroxyindolizidines. Similarly, the two xylo-configured major isoxazolidine derivatives were converted into the known derivatives (2R,6S,7R,8R,8aS)- and (2S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxyindolizidines. The six isomeric indolizidine derivatives obtained have been evaluated for their inhibiting activities towards 15 glycosidases. Only the (2R,6S,7S,8R,8aR)-configured isomer is a selective inhibitor of amyloglucosidases from Aspergillus niger (IC50 = 350 μM) and from Rhizopus mold (IC50 = 90 μM, Ki = 195 μM, non-competitive), the other indolizidines show very little inhibitory activity at 1 mM concentration.
Description19 páginas, 4 figuras, 2 tablas, 4 esquemas.
Publisher version (URL)http://dx.doi.org/10.1016/j.tetasy.2007.08.001
Appears in Collections:(IIQ) Artículos
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