Enantioselective Organocatalytic Construction of Hexahydropyrroloindole by Means of -Alkylation of Aldehydes Leading to the Total Synthesis of (+)-Gliocladin C

被引：123
|
作者：
Song, Jin [1 ,2 ]
Guo, Chang [1 ,2 ]
Adele, Arafate [1 ,2 ]
Yin, Hao [1 ,2 ]
Gong, Liu-Zhu [1 ,2 ]
机构：
[1] Univ Sci & Technol China, Microscale Joint Lab Green Synthet Chem, Hefei Natl Lab Phys Sci, Hefei 230026, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 10期
关键词：
alkaloids; amines; asymmetric catalysis; phosphoric acid; total synthesis; CONCISE TOTAL-SYNTHESIS; STEREOSELECTIVE ALPHA-ALKYLATION; ALPHA; BETA-UNSATURATED KETONES; CYCLOTRYPTAMINE ALKALOIDS; MICHAEL ADDITION; GENERAL-APPROACH; PHOSPHORIC-ACID; CATALYSIS; DERIVATIVES; EFFICIENT;
D O I：
10.1002/chem.201204522
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
12-Step program: The combined use of cinchona alkaloid based amine and chiral phosphoric acid enabled the asymmetric alkylation reaction of 3-hydroxyoxindoles with aldehydes to give 3,3′-disubstituted oxindoles in excellent enantioselectivities, which allows for the enantioselective total synthesis of (+)-gliocladin C in 12 steps from 3-hydroxyoxindole with 19 % overall yield (see scheme; PMB=para-methoxybenzyl). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：3319 / 3323
页数：5
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