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Synlett 2011(4): 576-578  
DOI: 10.1055/s-0030-1259531
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Synthesis of 2,4,6-Trideoxy-4-(dimethylamino)-3-C-methyl-l-lyxohexopyranose (Lemonose)

Guillaume Bernadata, Nicolas Georgea, Cédric Couturiera, Géraldine Masson*a, Thierry Schlamab, Jieping Zhu*a,c
a Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France
Fax: +33(1)69077247; e-Mail: geraldine.masson@icsn.cnrs-gif.fr;
b RHODIA, Centre de Recherches et de Technologie de Lyon (CRTL), avenue des Frères Perret, BP 62, 69192 Saint-Fons Cedex, France
c Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne (EPFL), EPFL-SB-ISIC-LSPN, 1015 Lausanne, Switzerland
e-Mail: jieping.zhu@epfl.ch;
Further Information

Publication History

Received 22 December 2010
Publication Date:
08 February 2011 (online)

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Abstract

l-Lemonose, the glycosidic part of (-)-lemonomycin, has been synthesized in ten steps with 18% overall yield from d-threonine. The key steps are a double, highly diastereoselective Grignard addition to a Weinreb amide and a chemoselective oxidation of a primary alcohol in the presence of a secondary alcohol, a tertiary alcohol and a tertiary amine, leading directly to the lactol.

Key words

sugar - aminosugar - lemonomycin - lemonose tetra­hydroisoquinoline

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