Synthesis of methylene exoglycals using a modified Julia olefination

被引：54

作者：

Gueyrard, D ^{[1
]}

Haddoub, R ^{[1
]}

Salem, A ^{[1
]}

Bacar, NS ^{[1
]}

Goekjian, PG ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, UMR 5181, Lab Chim Organ 2, F-69622 Villeurbanne, France

来源：

SYNLETT | 2005年 / 03期

关键词：

glycals; olefination; carbohydrate; alkenes; lactones;

D O I：

10.1055/s-2005-862364

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new route to exomethylene sugars is reported. The use of a two-step coupling-elimination procedure allows successful Julia olefination of sugar-derived lactones.

引用

页码：520 / 522

页数：3

共 25 条

[1]

BALKEMORE PR, 2002, J CHEM SOC P1, V23, P2563

[2] A DIRECT SYNTHESIS OF OLEFINS BY REACTION OF CARBONYL-COMPOUNDS WITH LITHIO DERIVATIVES OF 2-[ALKYL-SULFONYL OR (2'-ALKENYL)-SULFONYL OR BENZYL-SULFONYL]-BENZOTHIAZOLES [J].

BAUDIN, JB ;

HAREAU, G ;

JULIA, SA ;

RUEL, O .

TETRAHEDRON LETTERS, 1991, 32 (09) :1175-1178

[3]

BAUDIN JB, 1993, B SOC CHIM FR, V130, P856

[4] CONVERSION OF 2,6-ANHYDRO-1-DEOXY-D-GALACTO-HEPT-1-ENITOL INTO 1-DEOXY-D-GALACTO-HEPTULOSE BY BETA-D-GALACTOSIDASE [J].

BROCKHAUS, M ;

LEHMANN, J .

CARBOHYDRATE RESEARCH, 1977, 53 (01) :21-31

[5] Detours en route to a total synthesis of (+)-cassiol [J].

Colombo, MI ;

Zinczuk, J ;

Bohn, ML ;

Rúveda, EA .

TETRAHEDRON-ASYMMETRY, 2003, 14 (06) :717-725

[6] A concise synthesis of (+)-cassiol [J].

Colombo, MI ;

Zinczuk, J ;

Mischne, MP ;

Rúveda, EA .

TETRAHEDRON-ASYMMETRY, 2001, 12 (09) :1251-1253

[7] METHYLENATION OF ALDONOLACTONES [J].

CSUK, R ;

GLANZER, BI .

TETRAHEDRON, 1991, 47 (09) :1655-1664

[8] EFFICIENT SYNTHESES OF D-PSICO-FURANOSES AND D-SORBO-FURANOSES [J].

FAIVREBUET, V ;

EYNARD, I ;

NGA, HN ;

DESCOTES, G ;

GROUILLER, A .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1993, 12 (03) :349-356

[9] Studies on the synthesis of C-glycoside sulfones as potential glycosyl transferase inhibitors [J].

Gervay, J ;

Flaherty, TM ;

Holmes, D .

TETRAHEDRON, 1997, 53 (48) :16355-16364

[10] A Ramberg-Backlund approach to exo-glycals [J].

Griffin, FK ;

Murphy, PV ;

Paterson, DE ;

Taylor, RJK .

TETRAHEDRON LETTERS, 1998, 39 (44) :8179-8182

← 1 2 3 →