Synthesis of the orienticin C M(2-4) macrocycle utilizing a nucleophilic aromatic substitution strategy

被引:60
作者
Evans, DA
Watson, PS
机构
[1] Department of Chemistry, Harvard University, Cambridge
基金
美国国家卫生研究院; 美国国家科学基金会;
关键词
D O I
10.1016/0040-4039(96)00582-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of the fully functionalized M(2-4) macrocyclic orienticin C subunit 5 is described utilizing a intramolecular nucleophilic aromatic substitution reaction. (C) 1996 Elsevier Science Ltd.
引用
收藏
页码:3251 / 3254
页数:4
相关论文
共 24 条
[1]   THE STRUCTURE AND MODE OF ACTION OF GLYCOPEPTIDE ANTIBIOTICS OF THE VANCOMYCIN GROUP [J].
BARNA, JCJ ;
WILLIAMS, DH .
ANNUAL REVIEW OF MICROBIOLOGY, 1984, 38 :339-357
[2]   THE FIRST EXAMPLES OF S(N)AR-BASED MACROCYCLIZATION - SYNTHESIS OF MODEL CARBOXYLATE-BINDING POCKETS OF VANCOMYCIN [J].
BEUGELMANS, R ;
ZHU, JP ;
HUSSON, N ;
BOISCHOUSSY, M ;
SINGH, GP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (04) :439-440
[3]   SNAR-BASED MACROCYCLIZATION - AN APPLICATION TO THE SYNTHESIS OF VANCOMYCIN FAMILY MODELS [J].
BEUGELMANS, R ;
SINGH, GP ;
BOISCHOUSSY, M ;
CHASTANET, J ;
ZHU, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5535-5542
[4]   A NEW ACCESS TO 14-MEMBERED MACROCYCLE - SYNTHESIS OF MODEL F-O-G RING OF TEICOPLANIN [J].
BEUGELMANS, R ;
BOURDET, S ;
ZHU, JP .
TETRAHEDRON LETTERS, 1995, 36 (08) :1279-1282
[5]   THE FIRST SYNTHESIS OF A MODEL BICYCLIC D-O-E-F-O-G RING OF TEICOPLANIN VIA SEQUENTIAL INTRAMOLECULAR SNAR REACTIONS [J].
BEUGELMANS, R ;
NEUVILLE, L ;
BOISCHOUSSY, M ;
ZHU, JP .
TETRAHEDRON LETTERS, 1995, 36 (48) :8787-8790
[6]  
BEUGELMANS R, 1995, TETRAHEDRON LETT, V36, P7081
[7]   Synthesis of appropriately functionalized vancomycin CD and DE ring systems [J].
Boger, DL ;
Borzilleri, RM ;
Nukui, S .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (24) :3091-3096
[8]  
BOISCHOUSSY M, 1995, TETRAHEDRON LETT, V36, P4781
[9]   ALKYL NITRITE-METAL HALIDE DEAMINATION REACTIONS .6. DIRECT SYNTHESIS OF ARENEDIAZONIUM TETRAFLUOROBORATE SALTS FROM AROMATIC-AMINES, TERT-BUTYL NITRITE, AND BORON-TRIFLUORIDE ETHERATE IN ANHYDROUS MEDIA [J].
DOYLE, MP ;
BRYKER, WJ .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (09) :1572-1574
[10]  
Evans D.A., 1994, GLYCOPEPTIDE ANTIBIO, Vfirst, P63