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

[1] REACTIONS OF KETEN ACETALS .7. TOTAL SYNTHESES OF TETRAMETHYL ETHERS OF 1-ACYL-2,4,5,7-TETRAHYDROXYANTHRAQUINONES RHODOLAMPROMETRIN AND RHODOCOMATULIN
BANVILLE, J
BRASSARD, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (17): : 1852 - 1856
[2] BROSSI A, 1960, HELV CHIM ACTA, V43, P207
[3] CORCORAN JW, 1975, ANTIBIOTICS, V3, P606
[4] SYNTHESIS OF DISODIUM PREPHENATE AND DISODIUM EPIPREPHENATE - STEREOCHEMISTRY OF PREPHENIC ACID AND AN OBSERVATION ON THE BASE-CATALYZED REARRANGEMENT OF PREPHENIC ACID TO PARA-HYDROXYPHENYLLACTIC ACID
DANISHEFSKY, S
HIRAMA, M
FRITSCH, N
CLARDY, J
[J]. 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
DANISHEFSKY, S
SINGH, RK
HARAYAMA, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (17) : 5810 - 5812
[6] TOTAL SYNTHESIS OF DISODIUM PREPHENATE
DANISHEFSKY, S
HIRAMA, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (23) : 7740 - 7741
[7] SYNTHESIS OF DL-EPIGRISEOFULVIN
DANISHEFSKY, S
ETHEREDGE, SJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (24) : 4604 - 4605
[8] DIELS-ALDER REACTIONS OF 1,1-DIMETHOXY-3-TRIMETHYLSILYLOXY-1,3-BUTADIENE
DANISHEFSKY, S
SINGH, RK
GAMMILL, RB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (02) : 379 - 380
[9] USE OF BETA-PHENYLSULFINYL-ALPHA,BETA-UNSATURATED CARBONYL DIENOPHILES IN DIELS-ALDER REACTIONS
DANISHEFSKY, S
HARAYAMA, T
SINGH, RK
[J]. 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
DANISHEFSKY, S
YAN, CF
SINGH, RK
GAMMILL, RB
MCCURRY, PM
FRITSCH, N
CLARDY, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) : 7001 - 7008

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