FREE-RADICAL ANNELATION IN THE SYNTHESIS OF BICYCLIC BETA-LACTAMS .7. A ONE-POT, 4-STEP, SEQUENTIAL REACTION

被引:53
作者
BOSCH, E [1 ]
BACHI, MD [1 ]
机构
[1] WEIZMANN INST SCI,DEPT ORGAN CHEM,IL-76100 REHOVOT,ISRAEL
关键词
D O I
10.1021/jo00073a005
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nonfused, alkynyl-beta-lactams 10 and 18 react with n-Bu3SnH to give tert-butyl carbaceph-2-em-4-carboxylate (11) and methyl 1-oxahomoceph-3-em-5-carboxylate (19), respectively, in a four-step, sequential radical reaction involving homolytic intermolecular addition, intramolecular hydrogen atom transfer, endo-intramolecular addition, and beta-elimination.
引用
收藏
页码:5581 / 5582
页数:2
相关论文
共 23 条
[1]   FREE-RADICAL ANNELATION IN THE SYNTHESIS OF BICYCLIC BETA-LACTAMS .3. SYNTHESIS OF 1-OXACEPHEM AND 1-OXAHOMOCEPHEM DERIVATIVES [J].
BACHI, MD ;
HOORNAERT, C .
TETRAHEDRON LETTERS, 1982, 23 (24) :2505-2508
[2]  
BACHI MD, 1987, TETRAHEDRON LETT, V28, P2637
[3]   FREE-RADICAL ANNELATION IN THE SYNTHESIS OF BICYCLIC BETA-LACTAMS .6. SYNTHESIS OF TERT-BUTYL 2-BENZYLIDENE-1-CARBAPENAM-3-CARBOXYLATE [J].
BACHI, MD ;
DEMESMAEKER, A ;
STEVENARTDEMESMAEKER, N .
TETRAHEDRON LETTERS, 1987, 28 (25) :2887-2888
[4]   FREE-RADICAL ANNELATION IN THE SYNTHESIS OF BICYCLIC BETA-LACTAMS .4. EXO VS ENDO CYCLIZATIONS IN THE CONSTRUCTION OF THE (+/-)-1-OXACEPHAM AND (+/-)-1-OXAHOMOCEPHAM SYSTEMS [J].
BACHI, MD ;
FROLOW, F ;
HOORNAERT, C .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (11) :1841-1849
[5]   FREE-RADICAL ANNELATION IN THE SYNTHESIS OF BICYCLIC BETA-LACTAMS .1. SYNTHESIS OF 8-OXO-5-OXA-1-AZABICYCLO[4.2.0]OCTANE AND 9-OXO-6-OXA-1-AZABICYCLO[5.2.0]NONANE DERIVATIVES [J].
BACHI, MD ;
HOORNAERT, C .
TETRAHEDRON LETTERS, 1981, 22 (28) :2689-2692
[7]  
BACHI MD, IN PRESS BIOORGANIC
[8]  
BACHI MD, 1989, RECENT ADV CHEM BETA
[9]  
BARNER N, 1988, THESIS WEIZMANN I SC
[10]  
BECKWITH ALJ, 1986, REV CHEM INTERMED, V7, P143