Ruthenium-promoted diaryl ether synthesis in the construction of the F-O-G ring system of a teicoplanin model

被引：22

作者：

Pearson, AJ ^{[1
]}

Belmont, PO ^{[1
]}

机构：

[1] Case Western Reserve Univ, Dept Chem, Cleveland, OH 44106 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 11期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)00030-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An end-game approach is described for the synthesis of glycopeptide antibiotics related to teicoplanin, using ruthenium-promoted diaryl ether formation, followed by cycloamidation. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1671 / 1675

页数：5

共 42 条

[1] 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

[2] 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

[3] Vancomycin CD and DE macrocyclization and atropisomerism studies [J].

Boger, DL ;

Castle, SL ;

Miyazaki, S ;

Wu, JH ;

Beresis, RT ;

Loiseleur, O .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (01) :70-80

[4] Diastereoselective total synthesis of the vancomycin aglycon with ordered atropisomer equilibrations [J].

Boger, DL ;

Miyazaki, S ;

Kim, SH ;

Wu, JH ;

Loiseleur, O ;

Castle, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3226-3227

[5] STUDIES DIRECTED TOWARD THE SYNTHESIS OF GLYCOPEPTIDE ANTIBIOTIC TEICOPLANIN - 1ST SYNTHESIS OF THE N-TERMINAL 14-MEMBERED RING [J].

CHAKRABORTY, TK ;

REDDY, GV .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (20) :5462-5469

[6] PENTAFLUOROPHENYL DIPHENYLPHOSPHINATE - A NEW EFFICIENT COUPLING REAGENT IN PEPTIDE CHEMISTRY [J].

CHEN, SQ ;

XU, JC .

TETRAHEDRON LETTERS, 1991, 32 (46) :6711-6714

[7] SYNTHESIS OF DIARYL ETHERS FROM TYROSINE DERIVATIVES [J].

CRIMMIN, MJ ;

BROWN, AG .

TETRAHEDRON LETTERS, 1990, 31 (14) :2017-2020

[8] Synthesis and conformational properties of the M(4-6)(5-7) bicyclic tetrapeptide common to the vancomycin antibiotics [J].

Evans, DA ;

Dinsmore, CJ ;

Ratz, AM ;

Evrard, DA ;

Barrow, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3417-3418

[9] Approaches to the synthesis of the vancomycin antibiotics. Synthesis of orienticin C (bis-dechlorovancomycin) aglycon [J].

Evans, DA ;

Barrow, JC ;

Watson, PS ;

Ratz, AM ;

Dinsmore, CJ ;

Evrard, DA ;

DeVries, KM ;

Ellman, JA ;

Rychnovsky, SD ;

Lacour, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3419-3420

[10]

Evans DA, 1998, ANGEW CHEM INT EDIT, V37, P2704, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2704::AID-ANIE2704>3.0.CO

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