A stereoselective transformation of (-)-shikimic acid into (3R,4S,5R,7R)-7-(hydroxymethyl)azepane-3,4,5-triol, a potential glycosidase inhibitor

A stereoselective synthesis of (3R,4S,5R,7R)-7-(hydroxymethyl)azepane-3,4,5-triol hydrochloride from (-)-shikimic acid is described. The method involves the transformation of (-)-shikimic acid into (4S,5R)2,2-dimethyl-5((R)-1',4'-di(tert-butyldimethylsilyl)oxy-3'-oxobutyl)-1,3-dioxolane-4-carbaldehyde 9b, followed by a double reductive amination of this dicarbonyl compound to the final product. (C) 2015 Elsevier Ltd. All rights reserved.