PREPARATION OF CHIRAL 3-UNSUBSTITUTED BETA-LACTAMS FROM 3-HYDROXY BETA-LACTAMS BY USING THE ALKOXYKETENE-IMINE CYCLOADDITION REACTION AS AN APPROACH TO THE AZETIDINONE RING - A FORMAL SYNTHESIS OF THE CARBAPENEM ANTIBIOTIC (+)-PS-5

被引:53
作者
PALOMO, C
COSSIO, FP
ONTORIA, JM
ODRIOZOLA, JM
机构
[1] Departamento de Química Orgánica. Facultad, Química. Universidad
关键词
D O I
10.1016/0040-4039(91)80701-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Formation of chiral 3-hydroxy beta-lactams from the alkoxyketene-imine cycloaddition reaction followed by deoxygenation under Barton's conditions provided a simple route to optically active 3-unsubstituted beta-lactams.
引用
收藏
页码:3105 / 3108
页数:4
相关论文
共 35 条
[1]  
ALCAIDE B, 1986, HETEROCYCLES, V24, P1579
[2]   NEW AND SELECTIVE REACTIONS AND REAGENTS IN CARBOHYDRATE-CHEMISTRY [J].
BARTON, DHR ;
MOTHERWELL, WB .
PURE AND APPLIED CHEMISTRY, 1981, 53 (01) :15-31
[3]   NEW METHOD FOR DEOXYGENATION OF SECONDARY ALCOHOLS [J].
BARTON, DHR ;
MCCOMBIE, SW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (16) :1574-1585
[4]  
BIEG T, 1985, SYNTHESIS-STUTTGART, P76
[5]  
BROWN MJ, 1989, HETEROCYCLES, V29, P2225
[6]   BETA-LACTAMS FROM ESTER ENOLATES AND SILYLIMINES - ENANTIOSELECTIVE SYNTHESIS OF (+)-PS-5 [J].
CAINELLI, G ;
PANUNZIO, M ;
GIACOMINI, D ;
MARTELLI, G ;
SPUNTA, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6879-6880
[7]   CHIRAL CONTROL OF THE STAUDINGER REACTION [J].
COOPER, RDG ;
DAUGHERTY, BW ;
BOYD, DB .
PURE AND APPLIED CHEMISTRY, 1987, 59 (03) :485-492
[8]   THE ALPHA-BROMOESTER-IMINE CONDENSATION PROMOTED BY ZINC-TRIMETHYLCHLOROSILANE - A STEREOSPECIFIC SHORT FORMAL SYNTHESIS OF (+/-)-CARBAPENEM ANTIBIOTICS AND RELATED-COMPOUNDS [J].
COSSIO, FP ;
ODRIOZOLA, JM ;
OIARBIDE, M ;
PALOMO, C .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (02) :74-76
[9]  
ERNST B, Patent No. 3620467
[10]   THE ASYMMETRIC-SYNTHESIS OF BETA-LACTAM ANTIBIOTICS .5. APPLICATION OF CHIRAL ALPHA,BETA-EPOXYIMINES IN KETENE-IMINE CYCLO-ADDITION REACTIONS LEADING TO HOMOCHIRAL 3-AMINOAZETIDINONES [J].
EVANS, DA ;
WILLIAMS, JM .
TETRAHEDRON LETTERS, 1988, 29 (40) :5065-5068