通过烯炔闭环复分解串联反应合成抗肿瘤伊利多菌素核心结构的研究
Observations in the Synthesis of the Core of the Antitumor Illudins via an Enyne Ring Closing Metathesis Cascade.
作者信息
Movassaghi Mohammad, Piizzi Grazia, Siegel Dustin S, Piersanti Giovanni
机构信息
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
出版信息
Tetrahedron Lett. 2009 Sep 30;50(39):5489-5492. doi: 10.1016/j.tetlet.2009.07.102.
Abstract
Observations concerning the synthesis of the core spirocyclic AB-ring system of illudins using an enyne ring closing metathesis (EYRCM) cascade are discussed. Substituent effects, in addition to optimization of the reaction conditions and the olefin tether for the key EYRCM reaction, are examined.
摘要
讨论了关于使用烯炔关环复分解（EYRCM）串联反应合成伊利丁核心螺环AB环体系的观察结果。除了优化关键EYRCM反应的反应条件和烯烃连接基外，还研究了取代基效应。
相似文献
1
Observations in the Synthesis of the Core of the Antitumor Illudins via an Enyne Ring Closing Metathesis Cascade.通过烯炔闭环复分解串联反应合成抗肿瘤伊利多菌素核心结构的研究
Tetrahedron Lett. 2009 Sep 30;50(39):5489-5492. doi: 10.1016/j.tetlet.2009.07.102.
2
Photochemical Divergent Ring-Closing Metathesis of 1,7-Enynes: Efficient Synthesis of Spirocyclic Quinolin-2-ones.1,7-烯炔的光化学发散性闭环复分解反应：螺环喹啉-2-酮的高效合成
Org Lett. 2024 Aug 9;26(31):6664-6669. doi: 10.1021/acs.orglett.4c02332. Epub 2024 Jul 30.
3
Functional Metathesis Catalyst Through Ring Closing Enyne Metathesis: One Pot Protocol for Living Heterotelechelic Polymers.通过闭环烯炔复分解反应的功能转换催化剂：一锅法制备活异端基聚合物。
J Am Chem Soc. 2018 Mar 7;140(9):3181-3185. doi: 10.1021/jacs.7b12805. Epub 2018 Feb 22.
4
Multiple Olefin Metathesis Polymerization That Combines All Three Olefin Metathesis Transformations: Ring-Opening, Ring-Closing, and Cross Metathesis.多种烯烃复分解聚合反应，结合了三种烯烃复分解反应：开环、闭环和交叉复分解。
J Am Chem Soc. 2015 Jul 29;137(29):9262-5. doi: 10.1021/jacs.5b06033. Epub 2015 Jul 17.
5
Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives.用于合成紫杉烷和异紫杉烷衍生物的串联复分解反应
Chemistry. 2016 May 10;22(20):6891-8. doi: 10.1002/chem.201600592. Epub 2016 Apr 8.
6
Diversity-oriented approach to biologically relevant molecular frameworks starting with beta-naphthol and using the Claisen rearrangement and olefin metathesis as key steps.以β-萘酚为起始原料，采用克莱森重排和烯烃复分解反应作为关键步骤，构建具有生物学相关性分子骨架的多样性导向方法。
Chemistry. 2006 Oct 25;12(31):8024-38. doi: 10.1002/chem.200600540.
7
Domino ring-opening-ring-closing enyne metathesis vs enyne metathesis of norbornene derivatives with alkynyl side chains. Construction of condensed polycarbocycles.多米诺开环-闭环烯炔复分解反应与降冰片烯衍生物与炔基侧链的烯炔复分解反应。稠合多环碳环的构建。
Beilstein J Org Chem. 2018 Oct 25;14:2708-2714. doi: 10.3762/bjoc.14.248. eCollection 2018.
8
Development of an Enyne Metathesis/Isomerization/Diels-Alder One-Pot Reaction for the Synthesis of a Novel Near-Infrared (NIR) Dye Core.开发一种用于合成新型近红外（NIR）染料核心的烯炔复分解/异构化/狄尔斯-阿尔德一锅法反应。
Chemistry. 2015 Nov 23;21(48):17491-4. doi: 10.1002/chem.201502313. Epub 2015 Oct 9.
9
Synthesis of spirocyclic thiazolidinediones using ring-closing metathesis and one-pot sequential ring-closing/cross metathesis.使用关环复分解反应和一锅法串联关环/交叉复分解反应合成螺环噻唑烷二酮。
Org Biomol Chem. 2011 May 21;9(10):3801-7. doi: 10.1039/c0ob01248c. Epub 2011 Mar 28.
10
Synthesis of Stereocontrolled Degradable Polymer by Living Cascade Enyne Metathesis Polymerization.通过活性级联烯炔复分解聚合反应合成立体可控的可降解聚合物。
Angew Chem Int Ed Engl. 2023 Nov 13;62(46):e202312399. doi: 10.1002/anie.202312399. Epub 2023 Oct 9.
引用本文的文献
1
Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven.（-）-酰基富烯和（-）-irofulven 的对映选择性全合成。
J Org Chem. 2009 Dec 18;74(24):9292-304. doi: 10.1021/jo901926z.
本文引用的文献
1
Ovarian tumor growth regression using a combination of vascular targeting agents anginex or topomimetic 0118 and the chemotherapeutic irofulven.使用血管靶向药物血管抑素或拓扑模拟物0118与化疗药物伊洛福芬联合治疗使卵巢肿瘤生长消退。
Cancer Lett. 2008 Jul 8;265(2):270-80. doi: 10.1016/j.canlet.2008.02.048. Epub 2008 Apr 1.
2
Synergy of irofulven in combination with other DNA damaging agents: synergistic interaction with altretamine, alkylating, and platinum-derived agents in the MV522 lung tumor model.艾罗弗文与其他DNA损伤剂的协同作用：在MV522肺癌模型中与六甲蜜胺、烷化剂和铂类药物的协同相互作用。
Cancer Chemother Pharmacol. 2008 Dec;63(1):19-26. doi: 10.1007/s00280-008-0703-0. Epub 2008 Feb 28.
3
Quantitative correlation of drug bioactivation and deoxyadenosine alkylation by acylfulvene.酰基富烯对药物生物活化与脱氧腺苷烷基化的定量相关性
Chem Res Toxicol. 2007 Oct;20(10):1513-9. doi: 10.1021/tx7001756. Epub 2007 Sep 28.
4
Depurinating acylfulvene-DNA adducts: characterizing cellular chemical reactions of a selective antitumor agent.脱嘌呤酰基富烯-DNA加合物：表征一种选择性抗肿瘤剂的细胞化学反应
J Am Chem Soc. 2007 Feb 21;129(7):2101-11. doi: 10.1021/ja0665951. Epub 2007 Jan 27.
5
BRCA1 contributes to cell cycle arrest and chemoresistance in response to the anticancer agent irofulven.BRCA1有助于细胞周期停滞以及对抗癌药物艾瑞布林产生化学抗性。
Mol Pharmacol. 2007 Apr;71(4):1051-60. doi: 10.1124/mol.106.029504. Epub 2007 Jan 17.
6
Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven.（-）-酰基富烯和（-）-异罗氟芬的对映选择性全合成。
Angew Chem Int Ed Engl. 2006 Sep 4;45(35):5859-63. doi: 10.1002/anie.200602011.
7
Irofulven as first line therapy in recurrent or metastatic gastric cancer: a phase II multicenter study by the Cancer Therapeutics Research Group (CTRG).伊罗氟文作为复发性或转移性胃癌的一线治疗：癌症治疗研究组（CTRG）的一项II期多中心研究。
Cancer Chemother Pharmacol. 2007 Feb;59(3):295-300. doi: 10.1007/s00280-006-0270-1. Epub 2006 Jun 17.
8
Investigating the role of stereochemistry in the activity of anticancer acylfulvenes: synthesis, reductase-mediated bioactivation, and cellular toxicity.研究立体化学在抗癌酰基富烯活性中的作用：合成、还原酶介导的生物活化及细胞毒性
J Med Chem. 2006 Apr 20;49(8):2593-9. doi: 10.1021/jm051104t.
9
Production of Illudin M and of a Fourth Crystalline Compound by Clitocybe Illudens.亮盖伞产生伊利丁M和一种第四结晶化合物。
Proc Natl Acad Sci U S A. 1952 Nov;38(11):927-8. doi: 10.1073/pnas.38.11.927.
10
Total synthesis of (+)-beta-erythroidine.（+）-β-刺桐碱的全合成
Angew Chem Int Ed Engl. 2006 Apr 21;45(17):2731-4. doi: 10.1002/anie.200600210.
Zotero 插件