THE FIRST SYNTHESIS OF A MODEL BICYCLIC D-O-E-F-O-G RING OF TEICOPLANIN VIA SEQUENTIAL INTRAMOLECULAR SNAR REACTIONS

被引：24

作者：

BEUGELMANS, R ^{[1
]}

NEUVILLE, L ^{[1
]}

BOISCHOUSSY, M ^{[1
]}

ZHU, JP ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 48期

关键词：

D O I：

10.1016/0040-4039(95)01876-J

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A model bicyclic D-O-E-F-O-G ring (2) of teicoplanin (1) has been efficiently synthesized via sequential intramolecular SNAr reactions.

引用

页码：8787 / 8790

页数：4

共 45 条

[1] STRUCTURE ELUCIDATION OF THE TEICOPLANIN ANTIBIOTICS [J].

BARNA, JCJ ;

WILLIAMS, DH ;

STONE, DJM ;

LEUNG, TWC ;

DODDRELL, DM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (17) :4895-4902

[2] GLYCOPEPTIDE BINDING-SITE SPIED THROUGH TRANSFERRED HETERONUCLEAR NOE - [1-C-13]AC-D-ALA-D-ALA BONDED TO VANCOMYCIN AND RISTOCETIN-A [J].

BATTA, G ;

KOVER, KE ;

SZEKELY, Z ;

SZTARICSKAI, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2757-2758

[3] 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

[4] REDUCTIVE DEPROTECTION OF ARYL ALLYL ETHERS WITH PD(PH3)(4)/NABH4 [J].

BEUGELMANS, R ;

BOURDET, S ;

BIGOT, A ;

ZHU, JP .

TETRAHEDRON LETTERS, 1994, 35 (25) :4349-4350

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

BEUGELMANS, R ;

BIGOT, A ;

ZHU, JP .

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

[6] 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

[7] 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

[8] PALLADIUM-CATALYZED REDUCTIVE DEPROTECTION OF ALLOC - TRANSPROTECTION AND PEPTIDE-BOND FORMATION [J].

BEUGELMANS, R ;

NEUVILLE, L ;

BOISCHOUSSY, M ;

CHASTANET, J ;

ZHU, JP .

TETRAHEDRON LETTERS, 1995, 36 (18) :3129-3132

[9] VANCOMYCIN AND RISTOCETIN MODELS - SYNTHESIS VIA THE ULLMANN MACROCYCLIZATION REACTION [J].

BOGER, DL ;

NOMOTO, Y ;

TEEGARDEN, BR .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (06) :1425-1433

[10]

BOISCHOUSSY M, 1995, TETRAHEDRON LETT, V36, P4781

← 1 2 3 4 5 →