A Stereoselective Route toward Polyhydoxylated Piperidines. A Total Synthesis of (±)-Deoxymannojirimycin
- Resource Type
- Article
- Authors
- Boglio, C.; Stahlke, S.; Thorimbert, S.; Malacria, M.
- Source
- Organic Letters; October 2005, Vol. 7 Issue: 22 p4851-4854, 4p
- Subject
- Language
- ISSN
- 15237060; 15237052
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.