Total syntheses of the angucyclinone antibiotics (+)-emycin A and (+)-ochromycinone

被引：48

作者：

Larsen, DS

OShea, MD

Brooker, S

机构：

[1] Department of Chemistry, University of Otago, Dunedin

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 02期

关键词：

D O I：

10.1039/cc9960000203

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first asymmetric synthesis of the angucyclinone antibiotics, emycin A and ochromycinone, is achieved via a short, efficient sequence from 5-hydroxy-1,4-naphthoquinone with the key step being an effective kinetic resolution of a racemic diene in a Diels-Alder reaction promoted by a chiral Lewis acid derived from (S)-3,3'-diphenyl-1,1'-binaphthalene-2,2'-diol.

引用

收藏

页码：203 / 204

页数：2

相关论文

共 12 条

[1] ON THE INTERACTIVITY OF CHIRAL AUXILIARIES WITH CHIRAL CATALYSTS IN THE HETERO DIELS-ALDER REACTION - A NEW ROUTE TO L-GLYCOLIPIDS [J].

BEDNARSKI, M ;

DANISHEFSKY, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (23) :6968-6969

[2]

BOWIE JH, 1967, TETRAHEDRON LETT, P1449

[3] ASYMMETRIC AZA-DIELS-ALDER REACTION - ENANTIOSELECTIVE AND DIASTEREOSELECTIVE REACTION OF IMINE MEDIATED BY CHIRAL LEWIS ACID [J].

HATTORI, K ;

YAMAMOTO, H .

TETRAHEDRON, 1993, 49 (09) :1749-1760

[4] A RATIONALLY DESIGNED, CHIRAL LEWIS ACID FOR THE ASYMMETRIC INDUCTION OF SOME DIELS-ALDER REACTIONS [J].

KELLY, TR ;

WHITING, A ;

CHANDRAKUMAR, NS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) :3510-3512

[5] A STEREOSELECTIVE APPROACH TO THE ANGUCYCLINONE ANTIBIOTICS - A TOTAL SYNTHESIS OF THE C-1 EPIMER OF (+/-)-RUBIGINONE B1 [J].

LARSEN, DS ;

OSHEA, MD .

TETRAHEDRON LETTERS, 1993, 34 (08) :1373-1376

[6] A STEREOSELECTIVE APPROACH TO THE ANGUCYCLINONE ANTIBIOTICS - A TOTAL SYNTHESIS OF (+/-)-RUBIGINONE-B1 [J].

LARSEN, DS ;

OSHEA, MD .

TETRAHEDRON LETTERS, 1993, 34 (23) :3769-3772

[7] SYNTHETIC APPROACHES TO THE ANGUCYCLINE ANTIBIOTICS - THE TOTAL SYNTHESES OF (+/-)-RUBIGINONE-B-1 AND (+/-)-RUBIGINONE-B-2, (+/-)-EMYCIN-A, AND RELATED ANALOGS [J].

LARSEN, DS ;

OSHEA, MD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (08) :1019-1028

[8] ASYMMETRIC DIELS-ALDER REACTION DIRECTED TOWARD CHIRAL ANTHRACYCLINE INTERMEDIATES [J].

MARUOKA, K ;

SAKURAI, M ;

FUJIWARA, J ;

YAMAMOTO, H .

TETRAHEDRON LETTERS, 1986, 27 (40) :4895-4898

[9] ASYMMETRIC CATALYSIS OF DIELS-ALDER CYCLOADDITIONS BY AN MS-FREE BINAPHTHOL-TITANIUM COMPLEX - DRAMATIC EFFECT OF MS, LINEAR VS POSITIVE NONLINEAR RELATIONSHIP, AND SYNTHETIC APPLICATIONS [J].

MIKAMI, K ;

MOTOYAMA, Y ;

TERADA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (07) :2812-2820

[10] ANGUCYCLINE GROUP ANTIBIOTICS [J].

ROHR, J ;

THIERICKE, R .

NATURAL PRODUCT REPORTS, 1992, 9 (02) :103-137