Synthesis of the C14-C25 subunit of bafilomycin A1

被引：29

作者：

Eustache, F ^{[1
]}

Dalko, PI ^{[1
]}

Cossy, J ^{[1
]}

机构：

[1] ESPCI, CNRS, Chim Organ Lab, F-75231 Paris 05, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 26期

关键词：

D O I：

10.1021/jo035068m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of the C14-C25 subunit of bafilomycin A, was realized in a convergent route. The sequence involves two dynamic kinetic resolution steps of 2-alkyl 1,3-diketones that use optically active ruthenium complexes, an anti-selective reduction of a beta-hydroxyketone to control the C23 stereogenic center, and an aldol-type reaction under Evans' conditions, which sets the C17 and C18 stereogenic centers.

引用

页码：9994 / 10002

页数：9

共 60 条

[1] THE CONFORMATIONAL-ANALYSIS OF BAFILOMYCIN-A1
BAKER, GH
BROWN, PJ
DORGAN, RJJ
EVERETT, JR
[J]. 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
BAKER, GH
BROWN, PJ
DORGAN, RJJ
EVERETT, JR
LEY, SV
SLAWIN, AMZ
WILLIAMS, DJ
[J]. TETRAHEDRON LETTERS, 1987, 28 (45) : 5565 - 5568
[3] BAFILOMYCINS - A CLASS OF INHIBITORS OF MEMBRANE ATPASES FROM MICROORGANISMS, ANIMAL-CELLS, AND PLANT-CELLS
BOWMAN, EJ
SIEBERS, A
ALTENDORF, K
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1988, 85 (21) : 7972 - 7976
[4] CALTER MA, 1993, THESIS HARVARD U
[5] STEREOCHEMISTRY OF THE HYGROLIDINS
COREY, EJ
PONDER, JW
[J]. TETRAHEDRON LETTERS, 1984, 25 (39) : 4325 - 4328
[6] Cowden C. J., 1997, ORG REACTIONS, P1
[7] Enantioselective monoreduction of 2-alkyl-1,3-diketones mediated by chiral ruthenium catalysts. Dynamic kinetic resolution
Eustache, F
Dalko, PI
Cossy, J
[J]. ORGANIC LETTERS, 2002, 4 (08) : 1263 - 1265
[8] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE
EVANS, DA
CHAPMAN, KT
CARREIRA, EM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) : 3560 - 3578
[9] General strategies toward the syntheses of macrolide antibiotics. The total syntheses of 6-deoxyerythronolide B and oleandolide
Evans, DA
Kim, AS
Metternich, R
Novack, VJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (24) : 5921 - 5942
[10] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES
EVANS, DA
BARTROLI, J
SHIH, TL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) : 2127 - 2129

← 1 2 3 4 5 6 →