Highly Functionalized and Potent Antiviral Cyclopentane Derivatives Formed by a Tandem Process Consisting of Organometallic, Transition-Metal-Catalyzed, and Radical Reaction Steps

Pratap R. Jagtap; Leigh Ford; Elmar Deister; Radek Pohl; Ivana Císar?ová; Jan Hodek; Jan Weber; Richard Mackman; Gina Bahador; Ullrich Jahn

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Highly Functionalized and Potent Antiviral Cyclopentane Derivatives Formed by a Tandem Process Consisting of Organometallic, Transition-Metal-Catalyzed, and Radical Reaction Steps

机译：由有机金属，过渡金属催化和自由基反应步骤组成的串联过程形成的功能强大且有效的抗病毒环戊烷衍生物

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A simple modular tandem approach to multiply substituted cyclopentane derivatives is reported, which succeeds by joining organometallic addition, conjugate addition, radical cyclization, and oxygenation steps. The key steps enabling this tandem process are the thus far rarely used isomerization of allylic alkoxides to enolates and singleelectron transfer to merge the organometallic step with the radical and oxygenation chemistry. This controlled lineup of multiple electronically contrasting reactive intermediates provides versatile access to highly functionalized cyclopentane derivatives from very simple and readily available commodity precursors. The antiviral activity of the synthesized compounds was screened and a number of compounds showed potent activity against hepatitis C and dengue viruses.

机译：报道了一种简单的串联串联方法来多重取代的环戊烷衍生物，该方法通过加入有机金属加成，共轭加成，自由基环化和氧合步骤而成功。实现这种串联过程的关键步骤是迄今很少使用的烯丙基醇盐异构化为烯醇化物和单电子转移以将有机金属步骤与自由基和氧合化学结合在一起。多种电子对比反应性中间体的受控产品组合使人们能够从非常简单且容易获得的商品前体中广泛获得高度官能化的环戊烷衍生物。筛选了合成化合物的抗病毒活性，许多化合物显示出对丙型肝炎和登革热病毒的有效活性。

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《Chemistry: A European journal》 |2014年第33期|共7页
作者
Pratap R. Jagtap; Leigh Ford; Elmar Deister; Radek Pohl; Ivana Císar?ová; Jan Hodek; Jan Weber; Richard Mackman; Gina Bahador; Ullrich Jahn;
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正文语种 eng
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modular; tandem; approach;

机译：模块化;串联;方法;

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1. Highly Functionalized and Potent Antiviral Cyclopentane Derivatives Formed by a Tandem Process Consisting of Organometallic, Transition-Metal-Catalyzed, and Radical Reaction Steps [J] . Pratap R. Jagtap, Leigh Ford, Elmar Deister, Chemistry: A European journal . 2014,第33期

机译：由有机金属，过渡金属催化和自由基反应步骤组成的串联过程形成的功能强大且有效的抗病毒环戊烷衍生物
2. Highly enantioselective organocatalytic formation of functionalized cyclopentane derivatives via tandem conjugate addition/α-alkylation of enals [J] . Reme? M., Vesely J. European journal of organic chemistry . 2012,第20期

机译：通过对映体的串联共轭加成/α-烷基化对官能化环戊烷衍生物的高度对映选择性有机催化形成
3. Novel synthesis of highly functionalized cyclopentane derivatives via [3+2] cycloaddition reactions of donor-acceptor cyclopropanes and (E)-3-aryl-2-cyanoacrylates [J] . Dai Chenlu, Li Mingshuang, Chen Mengjun, Journal of chemical research: reviews and research papers from all branches of chemistry . 2019,第1a2期

机译：通过[3 + 2]循环加油反应的新型官能化环戊烷衍生物的新的合成供体 - 受体环烷基和（e）-3-芳基-2-氰基丙烯酸丙烯酸酯
4. Development of a Highly Sensitive Ultra-Performance Liquid Chromatography Tandem Mass Spectrometric Method for Quantitative Determination of Caffeic Acid Phenethyl Ester and its Fluorinated Derivative in Rat Plasma [C] . Jihai Pang, Xinyu Wang, Edward A. Felix, ASMS Conference on Mass Spectrometry and Allied Topics . 2008

机译：高敏感的超高效液相色谱串联质谱法，用于定量测定大鼠等离子体中咖啡酸苯乙烷的定量测定及其氟化衍生物
5. Toward an improved ring-forming method: I. 1,1-Dihalo-1-ethenyl vinylcyclopropanes--useful building blocks for the stereoselective synthesis of highly functionalized cyclopentanes. II. Further attempts toward the synthesis of the Brefeldin class of natura [D] . Berven, Heidi Marie. 1994

机译：寻求一种改进的成环方法：I. 1,1-二卤-1-乙烯基乙烯基环丙烷-有用的结构单元，用于立体选择性合成高度官能化的环戊烷。二。进一步尝试合成天然的布雷菲德丁类
6. Asymmetric Synthesis of Highly Functionalized Cyclopentanes by a Rhodium- and Scandium-Catalyzed Five-Step Domino Sequence [O] . Brendan T. Parr, Zhanjie Li, Huw M. L. Davies -1

机译：高度功能化的环戊烷的不对称合成由铑和钪催化五步骤多米诺序列
7. Recent Advance of Transition-Metal-Catalyzed Tandem Carboxylation Reaction of Unsaturated Hydrocarbons with Organometallic Reagents and CO2 [O] . Yaping Yi, Wei Hang, Chanjuan Xi 2021

机译：不饱和烃与有机金属试剂和CO2的过渡金属催化串联羧化反应的最近进展

Highly Functionalized and Potent Antiviral Cyclopentane Derivatives Formed by a Tandem Process Consisting of Organometallic, Transition-Metal-Catalyzed, and Radical Reaction Steps

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