General and efficient synthesis of β-lactams bearing a quinone moiety at N1, C3 or C4 positions

被引:16
作者
Alcaide, B [1 ]
Almendros, P [1 ]
Salgado, NR [1 ]
机构
[1] Univ Complutense, Fac Ciencias Quim, Dept Quim Inorgan 1, E-28040 Madrid, Spain
关键词
D O I
10.1016/S0040-4039(00)02298-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general and efficient synthesis of cis- and trans-beta -lactams bearing a quinone moiety at N1, C3 or C4 positions has been developed in a racemic form. In some cases this methodology offers the possibility of achieving the 2-azetidinone-quinone in an optically pure form. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1503 / 1505
页数:3
相关论文
共 16 条
[1]   Stereoselective allylation of 4-oxoazetidine-2-carbaldehydes.: Application to the stereocontrolled synthesis of fused tricyclic β-lactams via intramolecular Diels-Alder reaction of 2-azetidinone-tethered trienes [J].
Alcaide, B ;
Almendros, P ;
Salgado, NR .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3310-3321
[2]   Reverse-Cope elimination versus 1,3-dipolar cycloaddition in the reaction of enantiopure 2-azetidinone-tethered alkynylaldehydes with N-methylhydroxylamine [J].
Alcaide, B ;
Sáez, E .
TETRAHEDRON LETTERS, 2000, 41 (10) :1647-1651
[3]  
[Anonymous], 1993, ORGANIC CHEM BETA LA
[4]   REAGENTS AND SYNTHETIC METHODS .67. PREPARATION OF 4-UNSUBSTITUTED BETA-LACTAMS FROM 4-ACETOXYAZETIDIN-2-ONES - A FORMAL APPROACH TO MONOBACTAMS AND NOCARDINCINS [J].
ARRIETA, A ;
LECEA, B ;
COSSIO, FP ;
PALOMO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (16) :3784-3791
[5]  
BERSON J, 1988, CHEM QUINONOID COM 1, V2
[6]  
Bose K., 2000, AMIDE LINKAGE SELECT, P157
[7]   Diels-Alder reactions with 2-(arylsulfinyl)-1,4-benzoquinones:: Effect of aryl substitution on reactivity, chemoselectivity, and π-facial diastereoselectivity [J].
Carreño, MC ;
Ruano, JLG ;
Urbano, A ;
Remor, CZ ;
Arroyo, Y .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (02) :453-458
[8]   SYNTHETIC INHIBITORS OF ELASTASE [J].
EDWARDS, PD ;
BERNSTEIN, PR .
MEDICINAL RESEARCH REVIEWS, 1994, 14 (02) :127-194
[9]   THE ASYMMETRIC-SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .1. APPLICATION OF CHIRAL OXAZOLIDONES IN THE STAUDINGER REACTION [J].
EVANS, DA ;
SJOGREN, EB .
TETRAHEDRON LETTERS, 1985, 26 (32) :3783-3786
[10]  
Hoppen S, 2000, ANGEW CHEM INT EDIT, V39, P2099, DOI 10.1002/1521-3773(20000616)39:12<2099::AID-ANIE2099>3.0.CO