Journal
TETRAHEDRON-ASYMMETRY
Volume 26, Issue 5-6, Pages 320-323Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2015.02.005
Keywords
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Funding
- Spanish Ministry of Science and Innovation [CTQ2009-08490]
- Xunta de Galicia [CN2011/037]
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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.
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