A remarkably facile and stereochemically controlled fragmentation reaction in the hygrolide group of macrolide antibiotics

被引：18

作者：

Hanessian, S ^{[1
]}

Tehim, A ^{[1
]}

Meng, QC ^{[1
]}

Granberg, K ^{[1
]}

机构：

[1] ASTRA HASSLE AB,DEPT MED CHEM,S-43183 MOLNDAL,SWEDEN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 50期

关键词：

D O I：

10.1016/S0040-4039(96)02113-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of bafilomycin A(1) and isobafilomycin A(1) with triphenylphosphine and diethylazodicarboxylate under Mitsunobu conditions led to a fragmentation of the sugar-like ring to give the corresponding olefinic eater. The structure of the product from bafilomycin A(1) was confirmed by single crystal X-ray analysis and by H-1 NMR. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：9001 / 9004

页数：4

相关论文

共 21 条

[1] THE CONFORMATIONAL-ANALYSIS OF BAFILOMYCIN-A1 [J].

BAKER, GH ;

BROWN, PJ ;

DORGAN, RJJ ;

EVERETT, JR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (08) :1073-1079

[2] A CONFORMATIONAL STUDY OF BAFILOMYCIN-A1 BY X-RAY CRYSTALLOGRAPHY AND NMR TECHNIQUES [J].

BAKER, GH ;

BROWN, PJ ;

DORGAN, RJJ ;

EVERETT, JR ;

LEY, SV ;

SLAWIN, AMZ ;

WILLIAMS, DJ .

TETRAHEDRON LETTERS, 1987, 28 (45) :5565-5568

[3] CHEMISTRY OF UNUSUAL MACROLIDES .1. PREPARATION OF THE AGLYCONS OF CONCANAMYCIN-A AND ELAIOPHYLIN [J].

BINDSEIL, KU ;

ZEECK, A .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5487-5492

[4] BAFILOMYCINS - A CLASS OF INHIBITORS OF MEMBRANE ATPASES FROM MICROORGANISMS, ANIMAL-CELLS, AND PLANT-CELLS [J].

BOWMAN, EJ ;

SIEBERS, A ;

ALTENDORF, K .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (21) :7972-7976

[5] STEREOCHEMISTRY OF THE HYGROLIDINS [J].

COREY, EJ ;

PONDER, JW .

TETRAHEDRON LETTERS, 1984, 25 (39) :4325-4328

[6] CHEMICAL MODIFICATIONS OF BAFILOMYCIN-TYPE 16-MEMBERED DIENLACTONE MACROLIDES [J].

DEEG, M ;

HAGENMAIER, H ;

KRETSCHMER, A .

JOURNAL OF ANTIBIOTICS, 1987, 40 (03) :320-328

[7] INHIBITORY EFFECT OF MODIFIED BAFILOMYCINS AND CONCANAMYCINS ON P-TYPE AND V-TYPE ADENOSINE-TRIPHOSPHATASES [J].

DROSE, S ;

BINDSEIL, KU ;

BOWMAN, EJ ;

SIEBERS, A ;

ZEECK, A ;

ALTENDORF, K .

BIOCHEMISTRY, 1993, 32 (15) :3902-3906

[8]

GOETZ MA, 1985, ANTIBIOTICS, V38, P164

[9] DIE 1,4-ELIMINIERUNG UNTER FRAGMENTIERUNG [J].

GROB, CA ;

BAUMANN, W .

HELVETICA CHIMICA ACTA, 1955, 38 (03) :594-610

[10] MECHANISMS AND STEREOCHEMISTRY OF HETEROLYTIC FRAGMENTATION [J].

GROB, CA .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (08) :535-&