复分解级联策略（ROM-RCM-CM）：一种构建结构多样的磺内酰胺的DOS方法。
Metathesis Cascade Strategies (ROM-RCM-CM): A DOS approach to Skeletally Diverse Sultams.
作者信息
Jeon Kyu Ok, Rayabarapu Dinesh, Rolfe Alan, Volp Kelly, Omar Iman, Hanson Paul R
机构信息
Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045-7582.
出版信息
Tetrahedron. 2009 Jun 27;65(26):4992-5000. doi: 10.1016/j.tet.2009.03.080.
Abstract
The development of a ring-opening metathesis/ring-closing metathesis/cross metathesis (ROM-RCM-CM) cascade strategy to the synthesis of a diverse collection of bi- and tricyclic sultams is reported. In this study, functionalized sultam scaffolds derived from intramolecular Diels-Alder (IMDA) reactions undergo metathesis cascades to yield a collection tricyclic sultams. Additional appendage based diversity was achieved by utilizing a variety of CM partners.
摘要
报道了一种用于合成多种双环和三环磺内酰胺的开环复分解/闭环复分解/交叉复分解（ROM-RCM-CM）串联策略的开发。在本研究中，源自分子内狄尔斯-阿尔德（IMDA）反应的功能化磺内酰胺支架经历复分解串联反应，以产生一系列三环磺内酰胺。通过使用多种交叉复分解反应伙伴实现了基于附加基团的多样性。
相似文献
1
Metathesis Cascade Strategies (ROM-RCM-CM): A DOS approach to Skeletally Diverse Sultams.复分解级联策略（ROM-RCM-CM）：一种构建结构多样的磺内酰胺的DOS方法。
Tetrahedron. 2009 Jun 27;65(26):4992-5000. doi: 10.1016/j.tet.2009.03.080.
2
Triquinanes: a "one-pot" IMDA-tandem metathesis cascade strategy: ring-closing metathesis (RCM) dominates norbornene ROM!三萜烷：一锅法 IMDA 串联复分解级联策略：闭环复分解（RCM）主导降蒈烯 ROM！
Org Lett. 2010 Apr 16;12(8):1684-7. doi: 10.1021/ol100150f.
3
"Click, click, cyclize": a DOS approach to sultams utilizing vinyl sulfonamide linchpins.“咔嗒，咔嗒，环化”：一种利用乙烯基磺酰胺连接键合成磺内酰胺的DOS方法。
Org Lett. 2009 Feb 5;11(3):531-4. doi: 10.1021/ol802467f.
4
Synthesis of small molecules with high scaffold diversity: exploitation of metathesis cascades in combination with inter- and intramolecular Diels-Alder reactions.高骨架多样性小分子的合成：利用复分解级联反应与分子内和分子间 Diels-Alder 反应相结合。
Chemistry. 2010 Aug 16;16(31):9563-71. doi: 10.1002/chem.201000707.
5
Petasis Sequence Reactions for the Scaffold-Diverse Synthesis of Bioactive Polycyclic Small Molecules.用于生物活性多环小分子支架多样化合成的Petasis序列反应
ACS Omega. 2022 Dec 16;8(1):1168-1181. doi: 10.1021/acsomega.2c06585. eCollection 2023 Jan 10.
6
Molecular Acrobatics in Polycyclic Frames: Synthesis of "Kurmanediol" via Post-synthetic Modification of Cage Molecules by Olefinic Metathesis.多环骨架中的分子杂技：通过烯烃复分解对笼状分子进行后合成修饰合成“库曼二醇”
J Org Chem. 2023 Aug 18;88(16):11650-11660. doi: 10.1021/acs.joc.3c00968. Epub 2023 Jul 28.
7
8
Recent applications of ring-rearrangement metathesis in organic synthesis.环重排复分解反应在有机合成中的近期应用。
Beilstein J Org Chem. 2015 Oct 7;11:1833-64. doi: 10.3762/bjoc.11.199. eCollection 2015.
9
Application of RCM reaction in the construction of ABC ring of micrandilactone A.RCM反应在micrandilactone A的ABC环构建中的应用。
Org Lett. 2006 Jan 5;8(1):107-10. doi: 10.1021/ol052630h.
10
A diversity-oriented approach to spirocyclic and fused hydantoins via olefin metathesis.通过烯烃复分解反应实现稠合和螺环海因的多样性导向合成。
J Org Chem. 2012 Sep 21;77(18):8071-82. doi: 10.1021/jo301234r. Epub 2012 Sep 12.
引用本文的文献
1
Recent applications of ring-rearrangement metathesis in organic synthesis.环重排复分解反应在有机合成中的近期应用。
Beilstein J Org Chem. 2015 Oct 7;11:1833-64. doi: 10.3762/bjoc.11.199. eCollection 2015.
2
Exploring chemical diversity via a modular reaction pairing strategy.通过模块化反应配对策略探索化学多样性。
Beilstein J Org Chem. 2012;8:1293-302. doi: 10.3762/bjoc.8.147. Epub 2012 Aug 15.
3
Synthesis of a unique isoindoline/tetrahydroisoquinoline-based tricyclic sultam library utilizing a Heck-aza-Michael strategy.利用 Heck-aza-Michael 策略合成独特的异吲哚/四氢异喹啉三环磺内酰胺文库。
ACS Comb Sci. 2012 Mar 12;14(3):211-7. doi: 10.1021/co200181x. Epub 2012 Feb 6.
4
Synthesis of amino-benzothiaoxazepine-1,1-dioxides utilizing a microwave-assisted, S(N)Ar protocol.利用微波辅助的 S(N)Ar 反应协议合成氨基苯并噻唑-1,1-二氧化物。
ACS Comb Sci. 2011 Nov 14;13(6):653-8. doi: 10.1021/co200076j. Epub 2011 Sep 8.
5
A modular reaction pairing approach to the diversity-oriented synthesis of fused- and bridged-polycyclic sultams.一种模块化反应偶联方法，用于多样性导向合成稠合和桥连多环磺酰胺。
Org Lett. 2011 Oct 7;13(19):5148-51. doi: 10.1021/ol201962n. Epub 2011 Sep 7.
6
Synthesis of epoxybenzo[d]isothiazole 1,1-dioxides via a reductive-Heck, metathesis-sequestration protocol.通过还原-Heck、复分解-螯合协议合成环氧苯并[d]异噻唑 1,1-二氧化物。
Chem Commun (Camb). 2011 Sep 7;47(33):9528-30. doi: 10.1039/c1cc12503f. Epub 2011 Jul 5.
7
Synthesis of a stereochemically diverse library of medium-sized lactams and sultams via S(N)Ar cycloetherification.通过 S(N)Ar 环醚化反应合成具有立体化学多样性的中到大环内酰胺和内磺酰胺文库。
ACS Comb Sci. 2011 Jul 11;13(4):365-74. doi: 10.1021/co2000218. Epub 2011 Apr 28.
8
Automated synthesis of a 184-member library of thiadiazepan-1,1-dioxide-4-ones.自动化合成 184 个成员的噻二氮杂环戊烷-1,1-二氧化物-4-酮文库。
ACS Comb Sci. 2011 May 9;13(3):244-50. doi: 10.1021/co100060x. Epub 2011 Feb 10.
9
Scaling out by microwave-assisted, continuous flow organic synthesis (MACOS): multi-gram synthesis of bromo- and fluoro-benzofused sultams benzthiaoxazepine-1,1-dioxides.通过微波辅助连续流动有机合成（MACOS）进行放大：溴代和氟代苯并稠合磺内酰胺苯并噻唑嗪-1,1-二氧化物的多克级合成。
Chemistry. 2010 Sep 24;16(36):10959-62. doi: 10.1002/chem.201001651.
10
Microwave-assisted sequential one-pot protocol to benzothiadiazin-3-one-1,1-dioxides via a copper-catalyzed N-arylation strategy.通过铜催化的N-芳基化策略，采用微波辅助顺序一锅法合成苯并噻二嗪-3-酮-1,1-二氧化物。
Tetrahedron Lett. 2009 Dec 16;50(50):6935-6937. doi: 10.1016/j.tetlet.2009.09.090.
本文引用的文献
1
Regioselective Domino Metathesis of Unsymmetrical 7-Oxanorbornenes with Electron-Rich Vinyl Acetate toward Biologically Active Glutamate Analogues.不对称7-氧杂降冰片烯与富电子醋酸乙烯酯的区域选择性多米诺复分解反应合成生物活性谷氨酸类似物
European J Org Chem. 2009 Nov 1;2009(32):5531-5548. doi: 10.1002/ejoc.200900580.
2
Regioselective Domino Metathesis of 7-Oxanorbornenes and Its Application to the Synthesis of Biologically Active Glutamate Analogues.7-氧杂降冰片烯的区域选择性多米诺复分解反应及其在生物活性谷氨酸类似物合成中的应用
European J Org Chem. 2008 Nov;2008(31):5215-5220. doi: 10.1002/ejoc.200800704.
3
Domino Heck-Aza-Michael Reactions: A One-Pot, Sequential Three-Component Approach to 1,1-Dioxido-1,2-benzisothiazoline-3-acetic Acid.多米诺 Heck-氮杂-迈克尔反应：一种用于合成 1,1-二氧化-1,2-苯并异噻唑啉-3-乙酸的一锅法、连续三组分方法。
European J Org Chem. 2008(31):5254-5262. doi: 10.1002/ejoc.200800651.
4
A highly regioselective ring-opening metathesis-cross metathesis process modulated by the electronic effects of the cross metathesis partner: an entry to quaternary prolines.一种由交叉复分解反应伙伴的电子效应调节的高度区域选择性的开环复分解-交叉复分解反应过程：通往季碳脯氨酸的途径。
J Org Chem. 2009 Feb 20;74(4):1736-9. doi: 10.1021/jo802399k.
5
"Click, click, cyclize": a DOS approach to sultams utilizing vinyl sulfonamide linchpins.“咔嗒，咔嗒，环化”：一种利用乙烯基磺酰胺连接键合成磺内酰胺的DOS方法。
Org Lett. 2009 Feb 5;11(3):531-4. doi: 10.1021/ol802467f.
6
Synthesis of natural-product-like molecules with over eighty distinct scaffolds.具有八十多种不同骨架的类天然产物分子的合成。
Angew Chem Int Ed Engl. 2009;48(1):104-9. doi: 10.1002/anie.200804486.
7
Exploiting domino enyne metathesis mechanisms for skeletal diversity generation.利用多米诺烯炔复分解反应机制生成骨架多样性。
Chem Commun (Camb). 2008 Jul 14(26):3001-3. doi: 10.1039/b807278g. Epub 2008 Jun 3.
8
Synthesis of sultam scaffolds via intramolecular oxa-Michael and diastereoselective Baylis-Hillman reactions.通过分子内氧杂-迈克尔反应和非对映选择性贝利斯-希尔曼反应合成磺内酰胺骨架。
Org Lett. 2008 Jul 17;10(14):2951-4. doi: 10.1021/ol8009072. Epub 2008 Jun 14.
9
Diversity-oriented synthesis; a spectrum of approaches and results.面向多样性的合成；一系列方法与成果。
Org Biomol Chem. 2008 Apr 7;6(7):1149-58. doi: 10.1039/b719372f. Epub 2008 Feb 19.
10
Anti-MRSA agent discovery using diversity-oriented synthesis.利用多样性导向合成发现抗耐甲氧西林金黄色葡萄球菌药物
Angew Chem Int Ed Engl. 2008;47(15):2808-12. doi: 10.1002/anie.200705415.
Zotero 插件