C-Glycoside formation via Lewis acid promoted reaction of O-glycosylimidates with pyrroles

被引:17
作者
Armitt, DJ
Banwell, MG [1 ]
Freeman, C
Parish, CR
机构
[1] Australian Natl Univ, Inst Adv Studies, Res Sch Chem, Canberra, ACT 0200, Australia
[2] Australian Natl Univ, Inst Adv Studies, John Curtin Sch Med Res, Canberra, ACT 0200, Australia
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2002年 / 15期
关键词
D O I
10.1039/b205690a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
O-Glycosylimidates such as 1 react with pyrroles in the presence of BF3.Et2O to give C-glycosides, e. g. 2, that are readily elaborated to congeners such as 12 and 13.
引用
收藏
页码:1743 / 1745
页数:3
相关论文
共 39 条
[1]  
ACBISCHER B, 1983, HELV CHIM ACTA, V66, P2210
[2]   Convergent syntheses of the pyrrolic marine natural products lamellarin-O, lamellarin-Q, lukianol-A and some more highly oxygenated congeners [J].
Banwell, MG ;
Flynn, BL ;
Hamel, E ;
Hockless, DCR .
CHEMICAL COMMUNICATIONS, 1997, (02) :207-208
[3]  
BANWELL MG, UNPUB EUR J ORG CHEM
[4]   Emerging roles of carbohydrates and glycomimetics in anticancer drug design [J].
Barchi, JJ .
CURRENT PHARMACEUTICAL DESIGN, 2000, 6 (04) :485-501
[5]  
Beau JM, 1997, TOP CURR CHEM, V187, P1
[6]  
BRAUNS A, 1929, J AM CHEM SOC, V51, P1800
[7]   N-(TRIISOPROPYLSILYL)PYRROLE - A PROGENITOR PAR EXCELLENCE OF 3-SUBSTITUTED PYRROLES [J].
BRAY, BL ;
MATHIES, PH ;
NAEF, R ;
SOLAS, DR ;
TIDWELL, TT ;
ARTIS, DR ;
MUCHOWSKI, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) :6317-6328
[8]  
Danishefsky SJ, 2000, ANGEW CHEM INT EDIT, V39, P836, DOI 10.1002/(SICI)1521-3773(20000303)39:5<836::AID-ANIE836>3.0.CO
[9]  
2-I
[10]   Synthesis of alpha- and beta-D-(1->-6)-C-disaccharides by Wittig olefination of formyl C-glycosides with glycopyranose 6-phosphoranes [J].
Dondoni, A ;
Zuurmond, HM ;
Boscarato, A .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8114-8124