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 [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]

CALTER MA, 1993, THESIS HARVARD U

[5] STEREOCHEMISTRY OF THE HYGROLIDINS [J].

COREY, EJ ;

PONDER, JW .

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 [J].

Eustache, F ;

Dalko, PI ;

Cossy, J .

ORGANIC LETTERS, 2002, 4 (08) :1263-1265

[8] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].

EVANS, DA ;

CHAPMAN, KT ;

CARREIRA, EM .

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 [J].

Evans, DA ;

Kim, AS ;

Metternich, R ;

Novack, VJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (24) :5921-5942

[10] ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. ERYTHRO-SELECTIVE CHIRAL ALOL CONDENSATIONS VIA BORON ENOLATES [J].

EVANS, DA ;

BARTROLI, J ;

SHIH, TL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (08) :2127-2129

← 1 2 3 4 5 6 →