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.

被引:20
作者
Afonso, A
Rosenblum, SB
Puar, MS
McPhail, AT
机构
[1] Schering Plough Corp, Inst Res, Kenilworth, NJ 07033 USA
[2] Duke Univ, Paul M Gross Chem Lab, Durham, NC 27706 USA
关键词
D O I
10.1016/S0040-4039(98)01648-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phenanthridines 4 and the 11H-dibenzo[b,e]azepin-11-one 17 were used as the imine components in the ketene-imine beta-lactam synthesis to provide the fused tetracyclic beta-lactams 7, 8 and 18. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7431 / 7434
页数:4
相关论文
共 8 条
[1]  
BEVAN FM, 1989, J CHEM RES-S, P116
[2]   TRANS DIASTEREOSELECTIVE SYNTHESIS OF 3-ALKYL SUBSTITUTED BETA-LACTAMS VIA THE ACID CHLORIDE-IMINE REACTION OF NONACTIVATED ACID-CHLORIDES [J].
BROWNE, M ;
BURNETT, DA ;
CAPLEN, MA ;
CHEN, LY ;
CLADER, JW ;
DOMALSKI, M ;
DUGAR, S ;
PUSHPAVANAM, P ;
SHER, R ;
VACCARO, W ;
VIZIANO, M ;
ZHAO, HR .
TETRAHEDRON LETTERS, 1995, 36 (15) :2555-2558
[3]   2-AZETIDINONES AS INHIBITORS OF CHOLESTEROL ABSORPTION [J].
BURNETT, DA ;
CAPLEN, MA ;
DAVIS, HR ;
BURRIER, RE ;
CLADER, JW .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) :1733-1736
[4]   ACYLANTHRANILS .3. INFLUENCE OF RING SUBSTITUENTS ON REACTIVITY AND SELECTIVITY IN REACTION OF ACYLANTHRANILS WITH AMINES [J].
ERREDE, LA ;
OIEN, HT ;
YARIAN, DR .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (01) :12-18
[5]  
GEORG GI, 1992, ORGANIC CHEM BETA LA, pCH6
[6]  
GHOSEZ L, 1991, COMPREHENSIVE ORGANI, V5, P90
[7]   NEW ROUTES TO CONDENSED POLYNUCLEAR COMPOUNDS .7. SYNTHESIS OF PHENANTHRIDINES THROUGH A NOVEL CYCLIZATION REACTION OF HALOANILS [J].
KESSAR, SV ;
GOPAL, R ;
SINGH, M .
TETRAHEDRON, 1973, 29 (01) :167-175
[8]   Discovery of 1-(4-fluorophenyl)-(3R)-[3-(4-fluorophenyl)-(3S)-hydroxypropyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone (SCH 58235):: A designed, potent, orally active inhibitor of cholesterol absorption [J].
Rosenblum, SB ;
Huynh, T ;
Afonso, A ;
Davis, HR ;
Yumibe, N ;
Clader, JW ;
Burnett, DA .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (06) :973-980