Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from D-ribose

被引:17
作者
Argyropoulos, NG [1 ]
Panagiotidis, TD [1 ]
Gallos, JK [1 ]
机构
[1] Aristotle Univ Thessaloniki, Dept Chem, Thessaloniki 54124, Greece
关键词
D O I
10.1016/j.tetasy.2006.02.006
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of omega-oxo criciates from (D)-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:829 / 836
页数:8
相关论文
共 60 条
[1]   5-ENDO-TRIGONAL REACTIONS - DISFAVORED RING-CLOSURE [J].
BALDWIN, JE ;
CUTTING, J ;
DUPONT, W ;
KRUSE, L ;
SILBERMAN, L ;
THOMAS, RC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :736-738
[2]   RULES FOR RING-CLOSURE [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736
[3]   (PHENYLTHIO)NITROMETHANE IN THE TOTAL SYNTHESIS OF POLYOXIN-C [J].
BARRETT, AGM ;
LEBOLD, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3853-3857
[4]   X=Y-ZH systems as potential 1,3-dipoles.: Part 56:: Cascade 1,3-azaprotio cyclotransfer-cycloaddition reactions between aldoximes and divinyl ketone:: the effect of oxime E/Z isomerism on cycloaddition stereoselectivity [J].
Blackwell, M ;
Dunn, PJ ;
Graham, AB ;
Grigg, R ;
Higginson, P ;
Saba, IS ;
Thornton-Pett, M .
TETRAHEDRON, 2002, 58 (38) :7715-7725
[5]  
Breuer E., 1989, NITRONES NITRONATES, P139
[6]  
Broggini G, 1999, SYNTHESIS-STUTTGART, P905
[7]   Total syntheses of hyacinthacine A2 and 7-deoxycasuarine by cycloaddition to a carbohydrate derived nitrone [J].
Cardona, F ;
Faggi, E ;
Liguori, F ;
Cacciarini, M ;
Goti, A .
TETRAHEDRON LETTERS, 2003, 44 (11) :2315-2318
[8]   Synthesis and glycosidase inhibitory activity of 7-deoxycasuarine [J].
Carmona, AT ;
Whightman, RH ;
Robina, I ;
Vogel, P .
HELVETICA CHIMICA ACTA, 2003, 86 (09) :3066-3073
[9]   NEW SYNTHESIS OF 5-MEMBERED CYCLIC NITRONES FROM TARTARIC ACID [J].
CICCHI, S ;
HOLD, I ;
BRANDI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5274-5275
[10]   A 5-MEMBERED ENANTIOPURE CYCLIC NITRONE FROM MALIC-ACID BY REGIOSELECTIVE OXIDATION OF CYCLIC HYDROXYLAMINE - SYNTHESIS OF (1S,7S,8AR)-OCTAHYDRO-1,7-DIHYDROXYINDOLIZINE [J].
CICCHI, S ;
GOTI, A ;
BRANDI, A .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (15) :4743-4748