Access to enantiopure polycyclic β-lactams by Diels-Alder reaction of novel inner-outer-ring 2-(silyloxy)dienes with a carbacepham skeleton

被引:10
作者
Alcaide, B [1 ]
de Murga, RM [1 ]
Pardo, C [1 ]
Rodríguez-Ranera, C [1 ]
机构
[1] Univ Complutense Madrid, Fac Ciencias Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
关键词
beta-lactam; 2-azetidinone; carbacepham; diene; Diels-Alder cycloaddition;
D O I
10.1016/j.tetlet.2004.08.022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of unprecedented inner-outer-ring 2-[tert-butyidimethylsilyloxy]dienes with a carbacepham structure in optically pure form and their totally pi-facial endo selective Diels-Alder reactions to structurally novel polycyclic beta-lactams is reported. (C) 2004 Published by Elsevier Ltd.
引用
收藏
页码:7255 / 7259
页数:5
相关论文
共 45 条
[1]   Recent advances in the stereocontrolled synthesis of bi- and tricyclic-β-lactams with non-classical structure [J].
Alcaide, B ;
Almendros, P .
CURRENT ORGANIC CHEMISTRY, 2002, 6 (03) :245-264
[2]   Rapid entry to enantiopure carbacepham derivatives via Lewis acid promoted carbonyl-ene cyclization of 2-azetidinone-tethered alkenylaldehydes [J].
Alcaide, B ;
Pardo, C ;
Rodríguez-Ranera, C ;
Rodríguez-Vicente, A .
ORGANIC LETTERS, 2001, 3 (26) :4205-4208
[3]  
Alcaide B, 2002, SYNLETT, P381
[4]   4-Oxoazetidine-2-carbaldehydes as useful building blocks in stereocontrolled synthesis [J].
Alcaide, B ;
Almendros, P .
CHEMICAL SOCIETY REVIEWS, 2001, 30 (04) :226-240
[5]   Recent progress in the synthesis and reactivity of azetidine-2,3-diones. A review [J].
Alcaide, B ;
Almendros, P .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2001, 33 (04) :315-+
[6]   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
[7]  
ALCAIDE B, 2001, EUR J ORG CHEM
[8]  
[Anonymous], 1991, Comprehensive Organic Synthesis
[9]   Highly diastereoselective synthesis of 4-N-methylformamidino trinem (GV129606), a potent antibacterial agent [J].
Biondi, S ;
Pecunioso, A ;
Busi, F ;
Contini, SA ;
Donati, D ;
Maffeis, M ;
Pizzi, DA ;
Rossi, L ;
Rossi, T ;
Sabbatini, FM .
TETRAHEDRON, 2000, 56 (31) :5649-5655
[10]   Inhibition of human cytomegalovirus protease by monocyclic β-lactam derivatives:: Kinetic characterization using a fluorescent probe [J].
Bonneau, PR ;
Hasani, F ;
Plouffe, C ;
Malenfant, E ;
LaPlante, SR ;
Guse, I ;
Ogilvie, WW ;
Plante, R ;
Davidson, WC ;
Hopkins, JL ;
Morelock, MM ;
Cordingley, MG ;
Déziel, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :2965-2973