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A stereoselective route toward polyhydoxylated piperidines. A total synthesis of (±)-deoxymannojirimycin

Organic Letters, ISSN: 1523-7060, Vol: 7, Issue: 22, Page: 4851-4854
2005
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Article Description

(Chemical Equation Presented) A chemo- and stereoselective palladium-catalyzed amination of silylated butenediol dicarbonates has allowed for the introduction of a glycine moiety to obtain a desired functionalized epoxysilane. A stereoselective aldolization then delivered the piperidine ring which may be used as a precursor for the synthesis of a variety of polyhydroxylated azasugars. This efficient approach has been illustrated by the synthesis of 1-deoxymannojirimycin including a stereoselective reduction with LAH and a Tamao-Fleming oxidation of a C-SiMePh bond. © 2005 American Chemical Society.

Bibliographic Details

Boglio, Cécile; Stahlke, Sebastian; Thorimbert, Serge; Malacria, Max

American Chemical Society (ACS)

Biochemistry, Genetics and Molecular Biology; Chemistry

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