Total synthesis of bafilomycin A(1) .2. The assemblage and completion of the synthesis.

被引:52
作者
Toshima, K
Yamaguchi, H
Jyojima, T
Noguchi, Y
Nakata, M
Matsumura, S
机构
[1] Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama 223, 3-14-1 Hiyoshi, Kohoku-ku
关键词
D O I
10.1016/0040-4039(95)02351-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of the macrolide antibiotic, bafilomycin A(1) (1), has been achieved by a convergent route involving aldol condensation between the 16-membered lactonic aldehyde 2 and the ethyl ketone 3, followed by desilylation.
引用
收藏
页码:1073 / 1076
页数:4
相关论文
共 28 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]   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
[4]   STEREOSELECTIVE ALDOL REACTIONS WITH ALPHA-UNSUBSTITUTED CHIRAL ENOLATES [J].
BRAUN, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (01) :24-37
[5]   CHEMICAL MODIFICATIONS OF BAFILOMYCIN-TYPE 16-MEMBERED DIENLACTONE MACROLIDES [J].
DEEG, M ;
HAGENMAIER, H ;
KRETSCHMER, A .
JOURNAL OF ANTIBIOTICS, 1987, 40 (03) :320-328
[6]   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
[7]  
Evans D. A., 1982, TOP STEREOCHEM, V13, P1, DOI DOI 10.1002/9780470147221.CHL
[8]   STEREOSELECTIVE ALDOL CONDENSATIONS VIA BORON ENOLATES [J].
EVANS, DA ;
NELSON, JV ;
VOGEL, E ;
TABER, TR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (11) :3099-3111
[9]   DIASTEREOSELECTIVE ALDOL REACTIONS OF BETA-SILYLOXY ETHYL KETONES - APPLICATION TO THE TOTAL SYNTHESIS OF BAFILOMYCIN-A(1) [J].
EVANS, DA ;
CALTER, MA .
TETRAHEDRON LETTERS, 1993, 34 (43) :6871-6874
[10]  
GRELL W, 1966, LIEBIGS ANN CHEM, V699, P53