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Synlett 1997; 1997(11): 1294-1296
DOI: 10.1055/s-1997-5794
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Straightforward Synthesis of Pyrrolidine Glycosidase Inhibitors via Asymmetric Hetero-Diels-Alder Reaction

Albert Defoin* , Thierry Sifferlen, Jacques Streith
  • *École Nationale Supérieure de Chimie de Mulhouse, Université de Haute-Alsace, 3, rue Alfred Werner, 68093 Mulhouse Cédex, France, Fax (33) (0)3 89 43 77 90; E-mail: J.Streith@univ-mulhouse.fr
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Publication Date:
31 December 2000 (online)

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Base-catalysed rearrangement of the oxazine-carboxylate 8, obtained from pentadienoic acid 4 by asymmetric hetero-Diels-Alder reaction followed by simple chemical transformations, led to the protected trihydroxy-proline 9. Using various reduction conditions, the potent glycosidase inhibitors 1,4-dideoxy-1,4-imino-D-lyxitol D-1 and 1,4-dideoxy-1,4-imino-L-ribitol L-2 were obtained.

asymmetric Diels-Alder reaction - chiral nitroso derivative - (2S,3S,4R)-3,4-dihydroxyproline - 1,4-dideoxy-1,4-imino-D-lyxitol - 1,4-dideoxy-1,4-imino-L-ribitol