Asymmetric Synthesis of 2,4,6-Trideoxy-4-(dimethylamino)-3-C-methyl-Llyxohexopyranose (Lemonose)
Bernadat, Guillaume; George, Nicolas; Couturier, Cedric; Masson, Géraldine; Schlama, Thierry; Zhu, Jieping
2011

Abstract

L-Lemonose, the glycosidic part of (–)-lemonomycin, has been synthesized in ten steps with 18% overall yield from Dthreonine. 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.

Details

Title Asymmetric Synthesis of 2,4,6-Trideoxy-4-(dimethylamino)-3-C-methyl-Llyxohexopyranose (Lemonose)
Author(s) Bernadat, Guillaume ; George, Nicolas ; Couturier, Cedric ; Masson, Géraldine ; Schlama, Thierry ; Zhu, Jieping
Published in Synlett
Issue 4
Pages 576-578
Date 2011
Publisher Georg Thieme Verlag
ISSN 0936-5214
Keywords
DOI https://doi.org/10.1055/s-0030-1259531
Other identifier(s) View record in Web of Science
Laboratories LSPN
Record Appears in Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LSPN - Laboratory of synthesis and natural products
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published
Record creation date 2011-04-04