Stereoselective synthesis of novel five-membered homoazasugars. A convenient route to all-cis tetrasubstituted pyrrolidines |
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Authors: | Elena Moreno-Clavijo Antonio J. Moreno-Vargas |
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Affiliation: | Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Apartado 553, E-41071 Sevilla, Spain |
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Abstract: | ![]() We present a highly stereoselective procedure for the preparation of (2S and 2R,3S,4R,5S)-5-methyl-3,4-dihydroxy-2- ethoxycarbonylmethylpyrrolidines based on conjugate addition of ammonia to unsaturated aldonic esters derived from d-ribose followed by tandem cyclization. Derivatisation of these compounds to 2-hydroxyethyl-, benzymidazolylmethyl-, biphenyl-1-aminoethyl and naphthalene-l-aminoethyl-pyrrolidines is also presented. |
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Keywords: | Pyrrolidines Azasugars Iminosugars Imino-C-glycosides Homoazasugars Glycosidase inhibitors |
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