Download PDF
Synlett 1997; 1997(11): 1294-1296
DOI: 10.1055/s-1997-5794
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >