COMBINED DIRECTED METALATION - CROSS COUPLING STRATEGIES - A REGIOSPECIFIC ROUTE TO HETERORING-ANNELATED ORTHO-NAPHTHOQUINONES AND A SHORT SYNTHESIS OF BETA-LAPACHONE

被引：42

作者：

BRANDAO, MAF

DEOLIVEIRA, AB

SNIECKUS, V

机构：

[1] UNIV WATERLOO,GUELPH WATERLOO CTR GRAD WORK CHEM,WATERLOO N2L 3G1,ONTARIO,CANADA

[2] UNIV FED MINAS GERAIS,DEPT QUIM,BR-30000 BELO HORIZON,MG,BRAZIL

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 15期

关键词：

D O I：

10.1016/S0040-4039(00)60435-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general combined metalation - cross coupling methodology (Scheme 1) for the regiospecific construction of heteroring fused o-naphthoquinones 8 is described and its application to a short synthesis of the antimalarial/antitumor natural product beta-lapachone (14) is demonstrated.

引用

页码：2437 / 2440

页数：4

共 26 条

[1] SEQUENTIAL DIRECTED ORTHO METALATION BORONIC ACID CROSS-COUPLING REACTIONS - A GENERAL REGIOSPECIFIC ROUTE TO OXYGENATED DIBENZO[B,D]PYRAN-6-ONES RELATED TO ELLAGIC ACID
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[5] INHIBITION OF MICROSOMAL LIPID-PEROXIDATION AND CYTOCHROME-P-450-CATALYZED REACTIONS BY BETA-LAPACHONE AND RELATED NAPHTHOQUINONES
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VILLAMIL, SHF
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[6] THE DIRECTED ORTHO METALATION CONNECTION TO ARYL ARYL CROSS COUPLING - A GENERAL REGIOSPECIFIC SYNTHESIS OF PHENANTHROLS
FU, JM
SHARP, MJ
SNIECKUS, V
[J]. TETRAHEDRON LETTERS, 1988, 29 (43) : 5459 - 5462
[7] REMOTE AROMATIC METALATION - AN ANIONIC FRIEDEL-CRAFTS EQUIVALENT FOR THE REGIOSELECTIVE SYNTHESIS OF CONDENSED FLUORENONES FROM BIARYL AND META-TERARYL 2-AMIDES
FU, JM
ZHAO, BP
SHARP, MJ
SNIECKUS, V
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (05) : 1683 - 1685
[8] CONNECTIONS TO THE DIRECTED ORTHO METALATION STRATEGY - PD(0)-CATALYZED CROSS COUPLING OF ARYL BORONIC ACIDS WITH ARYL TRIFLATES
FU, JM
SNIECKUS, V
[J]. TETRAHEDRON LETTERS, 1990, 31 (12) : 1665 - 1668
[9] GRONOWITZ S, 1986, CHEM SCRIPTA, V26, P311
[10] GUPTA RB, 1990, SYNLETT, P355

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