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

被引：38
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.
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页码：4623 / 4626
页数：4
相关论文
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 [J].
COREY, EJ ;
GAVAI, AV .
TETRAHEDRON LETTERS, 1988, 29 (26) :3201-3204
[3]   SIMPLE ANALOGS OF GINKGOLIDE-B WHICH ARE HIGHLY-ACTIVE ANTAGONISTS OF PLATELET ACTIVATING FACTOR [J].
COREY, EJ ;
GAVAI, AV .
TETRAHEDRON LETTERS, 1989, 30 (50) :6959-6962
[4]   HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S .
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 [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S ;
CHEN, CP ;
SINGH, VK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7925-7926
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