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Synthesis 1997; 1997(6): 634-642
DOI: 10.1055/s-1997-3183
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Halocyclization and Palladium(II)-Catalyzed Amidocarbonylation of Unsaturated Aminopolypols. Synthesis of 1,4-Iminoglycitols as Potential Glycosidase Inhibitors

Walter Hümmer, Eric Dubois, Tibor Gracza, Volker Jäger*
  • *Institut für Organische Chemie der Universität Stuttgart, Pfaffenwladring 55, D-70569 Stuttgart, Germany, Fax +49(711)6854321; E-mail: jager.ioc@po.uni-stuttgart.de
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Publication Date:
31 December 2000 (online)

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Syntheses of optically active 2,5-anhydro-1,4-dideoxy-1,4-imino-D-lyxitol (6), 1,4,5-trideoxy-1,3-imino-D-lyxo-hexitol (14), and its N-methyl derivative 15 from achiral divinylcarbinol, via the aminopentenediol 1, are described using halogen-promoted cyclization and Pd(II)-catalyzed amidocarbonylation as key steps. 2,5,6-Trideoxy-2,5-imini-L-ido-heptitol (23), a diastereomeric homologue of the naturally occurring pyrrolidine DMDP G, is prepared from D-glucosamine hydrochloride in 7 steps in 19% overall yield. The new compounds 6, 14, 15, and 23 show weak glycosidase inhibition in two cases.

aminoalkenepolyols - polyhydroxlated pyrrolidines - glycosidase inhibitors - palladium(II) chloride catalysis - amidocarbonylation