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

被引：6

作者：

Bernadat, Guillaume ^{[1
]}

George, Nicolas ^{[1
]}

Couturier, Cedric ^{[1
]}

Masson, Geraldine ^{[1
]}

Schlama, Thierry ^{[2
]}

Zhu, Jieping ^{[1
,3
]}

机构：

[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France

[2] Ctr Rech & Technol Lyon CRTL, RHODIA, F-69192 St Fons, France

[3] Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, EPFL SB ISIC LSPN, CH-1015 Lausanne, Switzerland

来源：

SYNLETT | 2011年 / 04期

关键词：

sugar; aminosugar; lemonomycin; lemonose tetrahydroisoquinoline; AEROCOLONIGENES SUBSP ANTIBIOTICA; THIAZOLYL PEPTIDE ANTIBIOTICS; DESS-MARTIN PERIODINANE; IODOXYBENZOIC ACID IBX; SEBEKIA SP; GLYCOTHIOHEXIDE-ALPHA; MACROCYCLIC LACTONES; SELECTIVE OXIDATION; SECONDARY ALCOHOLS; (-)-LEMONOMYCIN;

D O I：

10.1055/s-0030-1259531

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：576 / 578

页数：3

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