Synthesis of a model bicyclic C-O-D-O-E ring of vancomycin by a one-pot, double SNAr based macrocyclization

被引：19

作者：

Beugelmans, R ^{[1
]}

BoisChoussy, M ^{[1
]}

Vergne, C ^{[1
]}

Bouillon, JP ^{[1
]}

Zhu, JP ^{[1
]}

机构：

[1] CNRS,INST CHIM SUBST NAT,F-91198 GIF SUR YVETTE,FRANCE

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 09期

关键词：

D O I：

10.1039/cc9960001029

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Double cyclization of linear pentapeptide 3 by treatment with CsF in DMF at -5 degrees C gives a model bicyclic CODOE ring 2 of vancomycin in a one-pot fashion.

引用

页码：1029 / 1030

页数：2

共 19 条

[1] 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

[2] A NOVEL SYNTHESIS OF K-13 [J].

BEUGELMANS, R ;

BIGOT, A ;

ZHU, JP .

TETRAHEDRON LETTERS, 1994, 35 (40) :7391-7394

[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] AN UNUSUALLY FACILE SNAR 14-MEMBERED BIARYL ETHER MACROCYCLIZATION REACTION SUITABLE FOR PREPARATION OF THE CYCLOISODITYROSINE SUBUNIT OF BOUVARDIN, DEOXYBOUVARDIN AND RELATED AGENTS [J].

BOGER, DL ;

BORZILLERI, RM .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (11) :1187-1190

[6]

BOISCHOUSSY M, 1995, TETRAHEDRON LETT, V36, P4781

[7] RESISTANCE OF ENTEROCOCCI TO GLYCOPEPTIDES [J].

COURVALIN, P .

ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1990, 34 (12) :2291-2296

[8]

EVAND DA, 1989, J AM CHEM SOC, V111, P8942

[9] THE ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS - ELECTROPHILIC AZIDATION OF CHIRAL IMIDE ENOLATES, A PRACTICAL APPROACH TO THE SYNTHESIS OF (R)-ALPHA-AZIDO AND (S)-ALPHA-AZIDO CARBOXYLIC-ACIDS [J].

EVANS, DA ;

BRITTON, TC ;

ELLMAN, JA ;

DOROW, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :4011-4030

[10] VANCOMYCIN - STRUCTURE AND TRANSFORMATION TO CDP-I [J].

HARRIS, CM ;

KOPECKA, H ;

HARRIS, TM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (23) :6915-6922

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