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A Stereoselective Route toward Polyhydoxylated Piperidines. A Total Synthesis of (±)-Deoxymannojirimycin

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journal contribution
posted on 27.10.2005, 00:00 by Cécile Boglio, Sebastian Stahlke, Serge Thorimbert, Max Malacria
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−SiMe2Ph bond.