A convenient trans-stereoselective synthesis of phenanthridine derived 2-azetidinones using the Staudinger ketene-imine cycloaddition

被引:31
作者
Alcaide, B [1 ]
Rodríguez-Vicente, A [1 ]
机构
[1] Univ Complutense, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
关键词
D O I
10.1016/S0040-4039(99)00102-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Staudinger reactions between acid chlorides having electron-withdrawing substituents at the alpha-position and phenanthridine, provide new fused tetracyclic 2-azetidinones in good yields with exclusive trans-stereoselectivity, both in racemic and enantiopure forms. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2005 / 2006
页数:2
相关论文
共 16 条
[1]   Beta-lactams derived from the reaction of phenanthridines and 11H-dibenzo[b,e]azepin-11-one with phenylvaleryl chloride.: Synthesis of fused analogs of the cholesterol absorption inhibitor Sch 48461. [J].
Afonso, A ;
Rosenblum, SB ;
Puar, MS ;
McPhail, AT .
TETRAHEDRON LETTERS, 1998, 39 (41) :7431-7434
[2]   New intramolecular cyclization and rearrangement processes based on the radical aryl-aryl coupling of arylsubstituted 2-azetidinones [J].
Alcaide, B ;
Rodríguez-Vicente, A .
TETRAHEDRON LETTERS, 1998, 39 (36) :6589-6592
[3]  
[Anonymous], 1995, ADV ASYMMETRIC SYNTH
[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]  
BURNETT DA, 1994, J MED CHEM, V37, P1933
[6]   2-azetidinone cholesterol absorption inhibitors: Structure-activity relationships on the heterocyclic nucleus [J].
Clader, JW ;
Burnett, DA ;
Caplen, MA ;
Domalski, MS ;
Dugar, S ;
Vaccaro, W ;
Sher, R ;
Browne, ME ;
Zhao, HR ;
Burrier, RE ;
Salisbury, B ;
Davis, HR .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (19) :3684-3693
[7]   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
[8]  
Georg G. I., 1993, The Organic Chemistry of (3-Lactams, P295, DOI [10.1002/chin.199425299, DOI 10.1002/CHIN.199425299]
[9]  
Hook V, 1997, CHEM BRIT, V33, P34
[10]  
MANHAS MS, 1988, HETEROCYCLES, V27, P1755