Halocyclization and Palladium(II)-Catalyzed Amidocarbonylation of Unsaturated Aminopolypols. Synthesis of 1,4-Iminoglycitols as Potential Glycosidase Inhibitors
- 1 June 1997
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1997 (06) , 634-642
- https://doi.org/10.1055/s-1997-3183
Abstract
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.Keywords
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