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

作者：Gonzalez Castro Marcos A; Poole Darren L; Estevez Juan C^*; Fleet George W J; Estevez Ramon J

来源：Tetrahedron: Asymmetry , 2015, 26(5-6): 320-323.

DOI：10.1016/j.tetasy.2015.02.005

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.

• 出版日期2015-3-28