ENANTIOSELECTIVE TOTAL SYNTHESIS OF GINKGOLIDE DERIVATIVES LACKING THE TERT-BUTYL GROUP, AN ESSENTIAL STRUCTURAL SUBUNIT FOR ANTAGONISM OF PLATELET-ACTIVATING-FACTOR

被引：37

作者：

COREY, EJ

RAO, KS

机构：

[1] Department of Chemistry, Harvard University, Cambridge

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 36期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(00)92265-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective total synthesis of the ginkgolide B analog 3 is reported along with the results of bioassays for antagonism of platelet activating factor. The three orders of magnitude difference in bioactivity of 2 and 3 demonstrates that the tert-butyl group of the ginkgolides is essential for anti-PAF potency.

引用

页码：4623 / 4626

页数：4

共 5 条

[1] BRAQUET P, 1987, Drugs of the Future, V12, P643
[2] ENANTIOSELECTIVE ROUTE TO A KEY INTERMEDIATE IN THE TOTAL SYNTHESIS OF GINKGOLIDE-B
COREY, EJ
GAVAI, AV
[J]. TETRAHEDRON LETTERS, 1988, 29 (26) : 3201 - 3204
[3] SIMPLE ANALOGS OF GINKGOLIDE-B WHICH ARE HIGHLY-ACTIVE ANTAGONISTS OF PLATELET ACTIVATING FACTOR
COREY, EJ
GAVAI, AV
[J]. TETRAHEDRON LETTERS, 1989, 30 (50) : 6959 - 6962
[4] HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS
COREY, EJ
BAKSHI, RK
SHIBATA, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) : 5551 - 5553
[5] A STABLE AND EASILY PREPARED CATALYST FOR THE ENANTIOSELECTIVE REDUCTION OF KETONES - APPLICATIONS TO MULTISTEP SYNTHESES
COREY, EJ
BAKSHI, RK
SHIBATA, S
CHEN, CP
SINGH, VK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) : 7925 - 7926

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