A HIGHLY ENANTIOSELECTIVE SYNTHESIS OF (R)-(-)-2-ACETYL-5,8-DIMETHOXY-1,2,3,4-TETRAHYDRO-2-NAPHTHOL - A KEY INTERMEDIATE IN THE SYNTHESIS OF ANTHRACYCLINONES

被引：31

作者：

DAVIS, FA

KUMAR, A

CHEN, BC

机构：

[1] Department of Chemistry, Drexel University, Philadelphia

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 07期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/S0040-4039(00)92107-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

AB-Synthon (R)-(-)-5, a key intermediate in the asymmetric synthesis of anthracyclinones 3 and 4 is prepared in 35% overall yield and > 95% ee. The key step involves hydroxylation of the potassium enolate of 7 using N-sulfonyloxaziridine (-)-6c.

引用

页码：867 / 870

页数：4

共 21 条

[1]

Arcamone F., 1982, DOXORUBICIN ANTICANC

[2]

BROADHURST MJ, 1985, CHEM IND-LONDON, P106

[3] ANTHRACYCLINES .2. INVESTIGATIONS RELATING TO THE SYNTHESIS OF 4-DEMETHOXYANTHRACYCLINONES [J].

BROADHURST, MJ ;

HASSALL, CH ;

THOMAS, GJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (09) :2239-2248

[4] ANTHRACYCLINES .1. THE SYNTHESIS OF RACEMIC DAUNOMYCINONE AND SOME RELATED TETRAHYDRONAPHTHACENEQUINONES [J].

BROADHURST, MJ ;

HASSALL, CH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (09) :2227-2238

[5] ENANTIOSELECTIVE SYNTHESIS OF TERTIARY ALPHA-HYDROXY CARBONYL-COMPOUNDS USING ((8,8-DICHLOROCAMPHORYL)SULFONYL)OXAZIRIDINE [J].

DAVIS, FA ;

WEISMILLER, MC .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3715-3717

[6] CHEMISTRY OF OXAZIRIDINES .14. ASYMMETRIC OXIDATION OF KETONE ENOLATES USING ENANTIOMERICALLY PURE (CAMPHORYLSULFONYL)OXAZIRIDINE [J].

DAVIS, FA ;

SHEPPARD, AC ;

CHEN, BC ;

HAQUE, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (18) :6679-6690

[7] APPLICATIONS OF OXAZIRIDINES IN ORGANIC-SYNTHESIS [J].

DAVIS, FA ;

SHEPPARD, AC .

TETRAHEDRON, 1989, 45 (18) :5703-5742

[8]

DAVIS FA, 1990, TETRAHEDRON LETT, P6823

[9]

DAVIS FA, IN PRESS J ORG CHEM

[10]

ELKHADEM HS, 1982, ANTHRACYCLINE ANTIBI

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