Published in
Elsevier, Tetrahedron: Asymmetry, 5-6(26), p. 320-323, 2015
DOI: 10.1016/j.tetasy.2015.02.005
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A stereoselective transformation of (−)-shikimic acid into (3R,4S,5R,7R)-7-(hydroxymethyl)azepane-3,4,5-triol, a potential glycosidase inhibitor
Journal article published in 2015 by
Marcos A. González Castro,
Darren L. Poole,
Juan C. Estévez,
George W. J. Fleet,
Ramón J. Estévez 
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Abstract
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.