Journal
TETRAHEDRON LETTERS
Volume 50, Issue 18, Pages 2045-2047Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.02.111
Keywords
L-Iminosugars; Polyhydroxylated piperidines; Glycosidase inhibitors; Dihydroxylation
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De novo synthesis of noncompetitive glycosidase inhibitors L-gulo-DNJ and L-talo-DNJ has been achieved in 9-10 steps starting from Garner's aldehyde. Key to the success of this procedure was the construction of the 2,3-unsaturated piperidine 14, which syn dihydroxylation under Kishi's and Donohoe's conditions led to the desired iminosugars. (c) 2009 Elsevier Ltd. All rights reserved.
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