乙烯型亚胺盐衍生物在海洋生物碱片螺素G三甲醚和宁加林B高效形式合成中的应用。
The application of vinylogous iminium salt derivatives to efficient formal syntheses of the marine akaloids lamellarin G trimethyl ether and ningalin B.
作者信息
Gupton John T, Giglio Benjamin C, Eaton James E, Rieck Elizabeth A, Smith Kristin L, Keough Matthew J, Barelli Peter J, Firich Lauren T, Hempel Jonathan E, Smith Timothy M, Kanters Rene P F
机构信息
Department of Chemistry, University of Richmond, Richmond, VA 23173, USA.
出版信息
Tetrahedron. 2009 May 30;65(22):4283-4292. doi: 10.1016/j.tet.2009.03.085.
Abstract
Studies directed at the synthesis of lamellarin G trimethyl ether and ningalin B via vinylogous iminium salt derivatives are described. The successful strategy relies on the formation of a 2,4-disubstituted pyrrole or a 1,2,3,4-tetrasubstituted pyrrole from a vinylogous iminium salt or vinylogous iminium salt derivative. Subsequent transformations of these highly substituted pyrroles lead to efficient and regiocontrolled formal syntheses of the respective pyrrole containing natural products.
摘要
描述了通过乙烯基类似亚胺盐衍生物合成片螺素G三甲醚和宁加林B的研究。成功的策略依赖于从乙烯基类似亚胺盐或乙烯基类似亚胺盐衍生物形成2,4-二取代吡咯或1,2,3,4-四取代吡咯。这些高度取代吡咯的后续转化导致了相应含吡咯天然产物的高效和区域选择性形式合成。
相似文献
1
The application of vinylogous iminium salt derivatives to efficient formal syntheses of the marine akaloids lamellarin G trimethyl ether and ningalin B.乙烯型亚胺盐衍生物在海洋生物碱片螺素G三甲醚和宁加林B高效形式合成中的应用。
Tetrahedron. 2009 May 30;65(22):4283-4292. doi: 10.1016/j.tet.2009.03.085.
2
The Application of Vinylogous Iminium Salt Derivatives and Microwave Accelerated Vilsmeier-Haack Reactions to Efficient Relay Syntheses of the Polycitone and Storniamide Natural Products.乙烯型亚胺盐衍生物和微波加速的维尔斯迈尔-哈克反应在多西托内酯和斯托尼酰胺天然产物高效接力合成中的应用
Tetrahedron. 2008;64(22):5246-5253. doi: 10.1016/j.tet.2008.03.038.
3
The application of formyl group activation of bromopyrrole esters to formal syntheses of lycogarubin C, permethyl storniamide A and lamellarin G trimethyl ether.溴代吡咯酯的甲酰基活化在石蒜黄素C、全甲基斯托尼酰胺A和片螺素G三甲醚的形式合成中的应用。
Tetrahedron. 2014 Dec 30;70(52):9759-9767. doi: 10.1016/j.tet.2014.11.035.
4
Scalable Total Syntheses of Some Natural and Unnatural Lamellarins: Application of a One-Pot Domino Process for Regioselective Access to the Central 1,2,4-Trisubstituted Pyrrole Core.一些天然和非天然 lamellarin 的可扩展全合成：一锅多步串联反应在区域选择性构建中央 1,2,4-三取代吡咯核中的应用。
J Org Chem. 2019 Sep 20;84(18):11596-11603. doi: 10.1021/acs.joc.9b01521. Epub 2019 Sep 4.
5
Synthesis of lactone-fused pyrroles by ruthenium-catalyzed 1,2-carbon migration-cycloisomerization.通过钌催化的 1,2-碳迁移-环化异构化合成内酯融合的吡咯。
Org Biomol Chem. 2019 Dec 18;18(1):81-85. doi: 10.1039/c9ob02363a.
6
Further studies on the application of vinylogous amides and β-halovinylaldehydes to the regiospecific synthesis of unsymmetrical, polyfunctionalized 2,3,4- and 1,2,3,4- substituted pyrroles.关于乙烯型酰胺和β-卤代乙烯醛在区域特异性合成不对称、多官能化的2,3,4-和1,2,3,4-取代吡咯中的应用的进一步研究。
Tetrahedron. 2018 May 24;74(21):2650-2663. doi: 10.1016/j.tet.2018.04.017. Epub 2018 Apr 7.
7
Application of vinylogous carbamates and vinylogous aminonitriles to the regiospecific synthesis of uniquely functionalized pyrroles and quinolones.乙烯型氨基甲酸酯和乙烯型氨基腈在独特官能化吡咯和喹诺酮区域特异性合成中的应用。
Tetrahedron. 2018 Dec 27;74(52):7408-7420. doi: 10.1016/j.tet.2018.10.078. Epub 2018 Nov 5.
8
Asymmetric Benzylic Functionalizations of 3-Vinyl Benzofurans via Cascade Formal Trienamine-Vinylogous Iminium Ion Activation.通过级联三烯胺-烯醇式亚胺离子活化实现 3-乙烯基苯并呋喃的不对称苄基官能化。
Org Lett. 2017 Sep 1;19(17):4652-4655. doi: 10.1021/acs.orglett.7b02287. Epub 2017 Aug 21.
9
Visible-Light-Promoted and Yb(OTf)3-Catalyzed Constructions of Coumarin-Pyrrole-(Iso)quinoline-Fused Pentacycles: Synthesis of Lamellarin Core, Lamellarin D Trimethyl Ether, and Lamellarin H.可见光照耀下和 Yb(OTf)3 催化构建香豆素-吡咯-(异)喹啉稠合五环体系：拉米那定核、拉米那定 D 三甲醚和拉米那定 H 的合成
Org Lett. 2016 Jan 15;18(2):332-5. doi: 10.1021/acs.orglett.5b03524. Epub 2016 Jan 7.
10
Regioselective preparation of 2-substituted 3,4-diaryl pyrroles: a concise total synthesis of ningalin B.2-取代的3,4-二芳基吡咯的区域选择性制备：宁加林B的简洁全合成
J Org Chem. 2002 Dec 27;67(26):9439-42. doi: 10.1021/jo026445i.
引用本文的文献
1
An Overview on the Synthesis of Lamellarins and Related Compounds with Biological Interest.层粘连蛋白及其具有生物活性的相关化合物的合成概述。
Molecules. 2024 Aug 26;29(17):4032. doi: 10.3390/molecules29174032.
2
Synthesis of Pyrrolopyrazinones by Construction of the Pyrrole Ring onto an Intact Diketopiperazine.通过在完整的二酮哌嗪上构建吡咯环合成吡咯并吡嗪酮。
J Org Chem. 2020 Jul 17;85(14):9264-9271. doi: 10.1021/acs.joc.0c01263. Epub 2020 Jun 30.
3
Application of vinylogous carbamates and vinylogous aminonitriles to the regiospecific synthesis of uniquely functionalized pyrroles and quinolones.乙烯型氨基甲酸酯和乙烯型氨基腈在独特官能化吡咯和喹诺酮区域特异性合成中的应用。
Tetrahedron. 2018 Dec 27;74(52):7408-7420. doi: 10.1016/j.tet.2018.10.078. Epub 2018 Nov 5.
4
Further studies on the application of vinylogous amides and β-halovinylaldehydes to the regiospecific synthesis of unsymmetrical, polyfunctionalized 2,3,4- and 1,2,3,4- substituted pyrroles.关于乙烯型酰胺和β-卤代乙烯醛在区域特异性合成不对称、多官能化的2,3,4-和1,2,3,4-取代吡咯中的应用的进一步研究。
Tetrahedron. 2018 May 24;74(21):2650-2663. doi: 10.1016/j.tet.2018.04.017. Epub 2018 Apr 7.
5
Anticancer properties of lamellarins.片螺素的抗癌特性。
Mar Drugs. 2015 Feb 19;13(3):1105-23. doi: 10.3390/md13031105.
6
The application of formyl group activation of bromopyrrole esters to formal syntheses of lycogarubin C, permethyl storniamide A and lamellarin G trimethyl ether.溴代吡咯酯的甲酰基活化在石蒜黄素C、全甲基斯托尼酰胺A和片螺素G三甲醚的形式合成中的应用。
Tetrahedron. 2014 Dec 30;70(52):9759-9767. doi: 10.1016/j.tet.2014.11.035.
7
Synthetic approaches to the lamellarins--a comprehensive review.片螺素的合成方法——全面综述
Mar Drugs. 2014 Dec 18;12(12):6142-77. doi: 10.3390/md12126142.
8
Formyl Group Activation of a Bromopyrrole Ester in Suzuki Cross-Coupling Reactions: Application to a Formal Synthesis of Polycitone A and B and Polycitrin A.铃木交叉偶联反应中溴代吡咯酯的甲酰基活化：在多西托宁A和B以及多西曲林A的形式合成中的应用
Tetrahedron. 2014 Apr 1;70(17):2738-2745. doi: 10.1016/j.tet.2014.02.091.
9
The application of (Z)-3-aryl-3-haloenoic acids to the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones.(Z)-3-芳基-3-卤代烯酸在(Z)-5-亚苄基-4-芳基吡咯-2(5H)-酮合成中的应用
Tetrahedron. 2010 Nov 20;66(47):9113-9122. doi: 10.1016/j.tet.2010.09.080.
本文引用的文献
1
Recent advances in lamellarin alkaloids: isolation, synthesis and activity.片螺素生物碱的最新进展：分离、合成与活性
Anticancer Agents Med Chem. 2008 Oct;8(7):746-60. doi: 10.2174/187152008785914789.
2
The Application of Vinylogous Iminium Salt Derivatives and Microwave Accelerated Vilsmeier-Haack Reactions to Efficient Relay Syntheses of the Polycitone and Storniamide Natural Products.乙烯型亚胺盐衍生物和微波加速的维尔斯迈尔-哈克反应在多西托内酯和斯托尼酰胺天然产物高效接力合成中的应用
Tetrahedron. 2008;64(22):5246-5253. doi: 10.1016/j.tet.2008.03.038.
3
Synthesis of lamellarin U and lamellarin G trimethyl ether by alkylation of a deprotonated alpha-aminonitrile.通过去质子化的α-氨基腈的烷基化反应合成片螺素U和片螺素G三甲醚。
J Org Chem. 2008 Jun 20;73(12):4526-31. doi: 10.1021/jo800467e. Epub 2008 May 24.
4
Lamellarins and related pyrrole-derived alkaloids from marine organisms.来自海洋生物的片螺素及相关吡咯衍生生物碱。
Chem Rev. 2008 Jan;108(1):264-87. doi: 10.1021/cr078199m. Epub 2007 Dec 21.
5
Docking and hydropathic scoring of polysubstituted pyrrole compounds with antitubulin activity.具有抗微管蛋白活性的多取代吡咯化合物的对接和亲水性评分
Bioorg Med Chem. 2008 Mar 1;16(5):2235-42. doi: 10.1016/j.bmc.2007.11.076. Epub 2007 Dec 4.
6
Synthesis and structure-activity relationship study of potent cytotoxic analogues of the marine alkaloid Lamellarin D.海洋生物碱片螺素D的高效细胞毒性类似物的合成及其构效关系研究
J Med Chem. 2006 Jun 1;49(11):3257-68. doi: 10.1021/jm0602458.
7
Lamellarins, from A to Z: a family of anticancer marine pyrrole alkaloids.片螺素，从A到Z：一类抗癌海洋吡咯生物碱。
Curr Med Chem Anticancer Agents. 2004 Jul;4(4):363-78. doi: 10.2174/1568011043352939.
8
A modular synthesis of the lamellarins: total synthesis of lamellarin G trimethyl ether.片螺素的模块化合成：片螺素G三甲醚的全合成。
J Org Chem. 2004 Apr 2;69(7):2362-6. doi: 10.1021/jo0352833.
9
Total synthesis of ningalin B utilizing a heterocyclic azadiene Diels-Alder reaction and discovery of a new class of potent multidrug resistant (MDR) reversal agents.利用杂环氮杂二烯狄尔斯-阿尔德反应全合成宁加林B并发现一类新型强效多药耐药（MDR）逆转剂。
J Org Chem. 2000 Apr 21;65(8):2479-83. doi: 10.1021/jo9916535.
10
Lamellarin alpha 20-sulfate, an inhibitor of HIV-1 integrase active against HIV-1 virus in cell culture.拉迈拉林α 20 - 硫酸盐，一种在细胞培养中对HIV - 1病毒有效的HIV - 1整合酶抑制剂。
J Med Chem. 1999 Jun 3;42(11):1901-7. doi: 10.1021/jm9806650.
Zotero 插件