STEREOSPECIFIC SYNTHESIS OF GRISEOFULVIN

被引：43

作者：

DANISHEFSKY, S

WALKER, FJ

机构：

[1] Contribution from the Department of Chemistry, University of Pittsburgh, 15260, Pittsburgh, Pennsylvania

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1979年 / 101卷 / 23期

关键词：

D O I：

10.1021/ja00517a040

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A total synthesis of griseofulvin has been achieved. The key step involved is a Diels-Alder cycloaddition between 1,1-dimethoxy-3-trimethyisilyloxy-1,3-butadiene (4) and 7-chloro-4,6-dimethoxy-2-(1-phenylsulfinylethylidene)-3(2H)-ben-zofuranone (20) to afford dl-5’,6’-dehydrogriseofulvin (13). © 1979, American Chemical Society. All rights reserved.

引用

页码：7018 / 7020

页数：3

共 17 条

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) :7013-7018

[5] DIELS-ALDER REACTIONS OF ALPHA-PHENYLSULFINYLMETHYLENECARBONYL COMPOUNDS - SYNTHESIS OF DISODIUM PREPHENATE DIMETHYL ACETAL [J].

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JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (17) :5810-5812

[6] TOTAL SYNTHESIS OF DISODIUM PREPHENATE [J].

DANISHEFSKY, S ;

HIRAMA, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (23) :7740-7741

[7] SYNTHESIS OF DL-EPIGRISEOFULVIN [J].

DANISHEFSKY, S ;

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JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (24) :4604-4605

[8] DIELS-ALDER REACTIONS OF 1,1-DIMETHOXY-3-TRIMETHYLSILYLOXY-1,3-BUTADIENE [J].

DANISHEFSKY, S ;

SINGH, RK ;

GAMMILL, RB .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (02) :379-380

[9] USE OF BETA-PHENYLSULFINYL-ALPHA,BETA-UNSATURATED CARBONYL DIENOPHILES IN DIELS-ALDER REACTIONS [J].

DANISHEFSKY, S ;

HARAYAMA, T ;

SINGH, RK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) :7008-7012

[10] DERIVATIVES OF 1-METHOXY-3-TRIMETHYLSILYLOXY-1,3-BUTADIENE FOR DIELS-ALDER REACTIONS [J].

DANISHEFSKY, S ;

YAN, CF ;

SINGH, RK ;

GAMMILL, RB ;

MCCURRY, PM ;

FRITSCH, N ;

CLARDY, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) :7001-7008

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