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Direct organocatalytic coupling of carboxylated piperazine-2,5-diones with indoles through conjugate addition of carbon nucleophiles to indolenine intermediates.通过碳亲核试剂对吲哚啉中间体的共轭加成实现羧化哌嗪 -2,5 -二酮与吲哚的直接有机催化偶联反应。
Tetrahedron Lett. 2010 Jan 27;51(4):609-612. doi: 10.1016/j.tetlet.2009.11.068.
2
Efficient Organocatalytic alpha-Sulfenylation of Substituted Piperazine-2,5-diones.取代哌嗪-2,5-二酮的高效有机催化α-亚磺酰化反应
Tetrahedron Lett. 2009 Jul 29;50(30):4310-4313. doi: 10.1016/j.tetlet.2009.05.031.
3
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Asymmetric organocatalytic synthesis of chiral 3,3-disubstituted oxindoles via a 1,6-conjugate addition reaction.通过 1,6-共轭加成反应不对称有机催化合成手性 3,3-二取代氧吲哚。
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Arenesulfonyl indole: new precursor for diversification of C-3 functionalized indoles.芳基磺酰基吲哚：用于C-3官能化吲哚多样化的新前体。
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Synthesis and stereochemical determination of an antiparasitic pseudo-aminal type monoterpene indole alkaloid.一种抗寄生虫伪氨基型单萜吲哚生物碱的合成及立体化学测定
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本文引用的文献

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Efficient Organocatalytic alpha-Sulfenylation of Substituted Piperazine-2,5-diones.取代哌嗪-2,5-二酮的高效有机催化α-亚磺酰化反应
Tetrahedron Lett. 2009 Jul 29;50(30):4310-4313. doi: 10.1016/j.tetlet.2009.05.031.
2
Direct inhibition of hypoxia-inducible transcription factor complex with designed dimeric epidithiodiketopiperazine.用设计的二聚体表二硫二肽抑制缺氧诱导因子复合物。
J Am Chem Soc. 2009 Dec 23;131(50):18078-88. doi: 10.1021/ja807601b.
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Total synthesis of (+)-11,11'-dideoxyverticillin A.（+）-11,11'-二脱氧轮枝菌素A的全合成
Science. 2009 Apr 10;324(5924):238-41. doi: 10.1126/science.1170777.
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Proline-catalyzed asymmetric formal alpha-alkylation of aldehydes via vinylogous iminium ion intermediates generated from arylsulfonyl indoles.脯氨酸催化的醛的不对称形式α-烷基化反应，该反应通过由芳基磺酰基吲哚生成的烯醇式亚胺离子中间体进行。
Angew Chem Int Ed Engl. 2008;47(45):8707-10. doi: 10.1002/anie.200803947.
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Concise total synthesis of (+)-WIN 64821 and (-)-ditryptophenaline.(+)-WIN 64821和(-)-二色胺的简洁全合成。
Angew Chem Int Ed Engl. 2008;47(8):1485-7. doi: 10.1002/anie.200704960.
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Simplified synthesis of 3-(1-arylsulfonylalkyl) indoles and their reaction with Reformatsky reagents.
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Enantioselective total synthesis of (+)-gliocladin C.（+）-绿胶霉素C的对映选择性全合成。
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8
Solventless clay-promoted Friedel-Crafts reaction of indoles with alpha-amido sulfones: unexpected synthesis of 3-(1-arylsulfonylalkyl) indoles.
Org Lett. 2006 Aug 31;8(18):4093-6. doi: 10.1021/ol061604w.
9
The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis.真菌毒素的表硫代二氧六环哌嗪（ETP）类：分布、作用方式、功能及生物合成
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Small molecule blockade of transcriptional coactivation of the hypoxia-inducible factor pathway.小分子对缺氧诱导因子途径转录共激活的阻断作用。
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通过碳亲核试剂对吲哚啉中间体的共轭加成实现羧化哌嗪 -2,5 -二酮与吲哚的直接有机催化偶联反应。

Direct organocatalytic coupling of carboxylated piperazine-2,5-diones with indoles through conjugate addition of carbon nucleophiles to indolenine intermediates.

作者信息

Dubey Ramin, Olenyuk Bogdan

机构信息

Department of Chemistry and Biochemistry, The University of Arizona, Tucson, AZ 85721.

出版信息

Tetrahedron Lett. 2010 Jan 27;51(4):609-612. doi: 10.1016/j.tetlet.2009.11.068.

DOI:10.1016/j.tetlet.2009.11.068
PMID:20161551
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2805156/
Abstract

The indole-diketopiperazine bridge is an important structural feature of many bispyrrolidinoindoline and epipolythiodiketopiperazine fungal metabolites. Organocatalytic conjugate addition of diketopiperazines to indoles was achieved in good to excellent yields through electrophilic indolenine intermediates generated under mild conditions. Screening of catalysts and solvents at different temperatures was performed in order to achieve high product yields.

摘要

吲哚-二酮哌嗪桥是许多双吡咯烷基吲哚啉和表聚硫代二酮哌嗪真菌代谢产物的重要结构特征。通过在温和条件下生成的亲电吲哚宁中间体，实现了二酮哌嗪对吲哚的有机催化共轭加成，产率良好至优异。为了获得高产物产率，在不同温度下对催化剂和溶剂进行了筛选。