Intramolecular reductive cyclization strategy to the synthesis of (-)-6-methyl-3-hydroxy-piperidine-2-carboxylic acid, (+)-6-methyl-(2-hydroxymethyl)-piperidine-3-ol and their glycosidase inhibitory activity.

Autor: Pawar VU; Garware Research Centre, Department of Chemistry, University of Pune, Pune 411007, India., Chavan ST, Sabharwal SG, Shinde VS
Jazyk: angličtina
Zdroj: Bioorganic & medicinal chemistry [Bioorg Med Chem] 2010 Nov 15; Vol. 18 (22), pp. 7799-803. Date of Electronic Publication: 2010 Oct 21.
DOI: 10.1016/j.bmc.2010.09.055
Abstrakt: The first stereoselective synthesis of (2S,3R,6S)-6-methyl-3-hydroxy-piperidine-2-carboxylic acid (-)-6 and (2R,3R,6S)-6-methyl-(2-hydroxymethyl)-piperidine-3-ol (+)-7 was achieved starting from readily available d-glucose in 14 steps with 17% overall yield for both the compounds. The key feature of the present strategy includes the Wittig-olefination for the preparation of required conjugated keto-azide 9 and construction of 2,3,6-trisubstituted piperidine skeleton 11 by applying intramolecular reductive cyclization of conjugated keto-azide intermediate. The glycosidase inhibitory activity of compounds 6 and 7 towards several glycosidases has been evaluated.
(Copyright © 2010 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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