• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

将烯炔复分解反应与成熟的有机转化反应相结合：一种用于生物活性分子可持续合成的强大策略。

Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules.

作者信息

Dragutan Valerian, Dragutan Ileana, Demonceau Albert, Delaude Lionel

机构信息

Institute of Organic Chemistry of the Romanian Academy, Bucharest, 060023, Romania.

Laboratory of Catalysis, Institut de Chimie (B6a), Allée du six Août 13, Université de Liège, 4000 Liège, Belgium.

出版信息

Beilstein J Org Chem. 2020 Apr 16;16:738-755. doi: 10.3762/bjoc.16.68. eCollection 2020.

DOI:10.3762/bjoc.16.68
PMID:32362948
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7176922/
Abstract

This account surveys the current progress on the application of intra- and intermolecular enyne metathesis as main key steps in the synthesis of challenging structural motifs and stereochemistries found in bioactive compounds. Special emphasis is placed on ruthenium catalysts as promoters of enyne metathesis to build the desired 1,3-dienic units. The advantageous association of this approach with name reactions like Grignard, Wittig, Diels-Alder, Suzuki-Miyaura, Heck cross-coupling, etc. is illustrated. Examples unveil the generality of such tandem reactions in providing not only the intricate structures of known, in vivo effective substances but also for designing chemically modified analogs as valid alternatives for further therapeutic agents.

摘要

本综述概述了分子内和分子间烯炔复分解反应作为关键步骤，在合成生物活性化合物中具有挑战性的结构基序和立体化学方面的当前进展。特别强调了钌催化剂作为烯炔复分解反应的促进剂，用于构建所需的1,3 - 二烯单元。阐述了这种方法与格氏反应、维蒂希反应、狄尔斯 - 阿尔德反应、铃木 - 宫浦反应、赫克交叉偶联反应等著名反应的有利结合。实例揭示了此类串联反应的普遍性，不仅能提供已知的体内有效物质的复杂结构，还能用于设计化学修饰的类似物，作为进一步治疗药物的有效替代品。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/cc8f15b73b94/Beilstein_J_Org_Chem-16-738-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/3648488a0d25/Beilstein_J_Org_Chem-16-738-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/edbb8bef7ccb/Beilstein_J_Org_Chem-16-738-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/b949852986f5/Beilstein_J_Org_Chem-16-738-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/43deefecb3da/Beilstein_J_Org_Chem-16-738-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/c2aa65fdd509/Beilstein_J_Org_Chem-16-738-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/3ac3e4ca86f8/Beilstein_J_Org_Chem-16-738-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/1e0c4fe79f04/Beilstein_J_Org_Chem-16-738-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/3dfbdfb169c5/Beilstein_J_Org_Chem-16-738-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/0096cc86a882/Beilstein_J_Org_Chem-16-738-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/48f271c0f62f/Beilstein_J_Org_Chem-16-738-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/79dbb658bad5/Beilstein_J_Org_Chem-16-738-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/12ce313d2209/Beilstein_J_Org_Chem-16-738-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/11c852026f4b/Beilstein_J_Org_Chem-16-738-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/db7ba46e1dff/Beilstein_J_Org_Chem-16-738-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/cc8f15b73b94/Beilstein_J_Org_Chem-16-738-g016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/3648488a0d25/Beilstein_J_Org_Chem-16-738-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/edbb8bef7ccb/Beilstein_J_Org_Chem-16-738-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/b949852986f5/Beilstein_J_Org_Chem-16-738-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/43deefecb3da/Beilstein_J_Org_Chem-16-738-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/c2aa65fdd509/Beilstein_J_Org_Chem-16-738-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/3ac3e4ca86f8/Beilstein_J_Org_Chem-16-738-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/1e0c4fe79f04/Beilstein_J_Org_Chem-16-738-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/3dfbdfb169c5/Beilstein_J_Org_Chem-16-738-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/0096cc86a882/Beilstein_J_Org_Chem-16-738-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/48f271c0f62f/Beilstein_J_Org_Chem-16-738-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/79dbb658bad5/Beilstein_J_Org_Chem-16-738-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/12ce313d2209/Beilstein_J_Org_Chem-16-738-g013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/11c852026f4b/Beilstein_J_Org_Chem-16-738-g014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/db7ba46e1dff/Beilstein_J_Org_Chem-16-738-g015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ddd/7176922/cc8f15b73b94/Beilstein_J_Org_Chem-16-738-g016.jpg

相似文献

1
Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules.将烯炔复分解反应与成熟的有机转化反应相结合：一种用于生物活性分子可持续合成的强大策略。
Beilstein J Org Chem. 2020 Apr 16;16:738-755. doi: 10.3762/bjoc.16.68. eCollection 2020.
2
Synergistic approach to polycycles through Suzuki-Miyaura cross coupling and metathesis as key steps.以铃木-宫浦交叉偶联和复分解为关键步骤的多环化合物协同合成方法。
Beilstein J Org Chem. 2018 Sep 21;14:2468-2481. doi: 10.3762/bjoc.14.223. eCollection 2018.
3
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.
4
Chemoselective olefin metathesis transformations mediated by ruthenium complexes.钌配合物介导的烯烃复分解化学选择性转化。
Chem Soc Rev. 2010 Aug;39(8):3305-16. doi: 10.1039/b912410c. Epub 2010 Jun 30.
5
Ring Rearrangement Metathesis in 7-Oxabicyclo[2.2.1]heptene (7-Oxanorbornene) Derivatives. Some Applications in Natural Product Chemistry.7-氧杂双环[2.2.1]庚烯（7-氧杂降冰片烯）衍生物中的环重排复分解反应。在天然产物化学中的一些应用。
Nat Prod Commun. 2017 May;12(5):713-732.
6
Design and Synthesis of Polycycles, Heterocycles, and Macrocycles via Strategic Utilization of Ring-Closing Metathesis.通过战略利用环 closing metathesis 设计和合成多环、杂环和大环。
Chem Rec. 2018 Nov;18(11):1613-1632. doi: 10.1002/tcr.201800025. Epub 2018 Jun 19.
7
Tandem enyne metathesis-Diels-Alder reaction for construction of natural product frameworks.用于构建天然产物骨架的串联烯炔复分解-狄尔斯-阿尔德反应。
J Org Chem. 2004 Mar 19;69(6):2084-93. doi: 10.1021/jo0356311.
8
Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2-pyrans.前手性氧杂二烯炔闭环复分解反应生成外消旋4-烯基-2-炔基-3,6-二氢-2-吡喃。
Beilstein J Org Chem. 2020 Nov 13;16:2757-2768. doi: 10.3762/bjoc.16.226. eCollection 2020.
9
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.
10
Application of an enyne metathesis/Diels-Alder cycloaddition sequence: a new versatile approach to the syntheses of C-aryl glycosides and spiro-C-aryl glycosides.烯炔复分解/Diels-Alder 环加成序列的应用：一种合成 C-芳基糖苷和螺 C-芳基糖苷的新方法。
Chemistry. 2010 Jul 26;16(28):8545-56. doi: 10.1002/chem.201000482.

引用本文的文献

1
Synthesis of mixed musks Eschenmoser-Tanabe fragmentation, enyne metathesis and Diels-Alder reaction as key steps.混合麝香的合成：以埃申莫泽-田边裂解反应、烯炔复分解反应和狄尔斯-阿尔德反应为关键步骤。
RSC Adv. 2022 May 11;12(22):14278-14281. doi: 10.1039/d2ra01458k. eCollection 2022 May 5.

本文引用的文献

1
Precision Aliphatic Polyesters via Cross-Metathesis Polymerization.通过交叉复分解聚合制备精密脂肪族聚酯
Curr Org Synth. 2019;16(2):188-204. doi: 10.2174/1570179416666181206095131.
2
Artemisinin-derived antimalarial endoperoxides from bench-side to bed-side: Chronological advancements and future challenges.青蒿素衍生的抗疟内过氧化物：从实验室到病床的历程进展和未来挑战。
Med Res Rev. 2020 Jul;40(4):1220-1275. doi: 10.1002/med.21657. Epub 2020 Jan 12.
3
Diversity-Oriented Approaches to Polycycles and Heterocycles via Enyne Metathesis and Diels-Alder Reaction as Key Steps.
以烯炔复分解反应和狄尔斯-阿尔德反应为关键步骤的多环和杂环化合物的多样性导向合成方法。
ACS Omega. 2019 Dec 16;4(27):22261-22273. doi: 10.1021/acsomega.9b03020. eCollection 2019 Dec 31.
4
Conformation of Tunable Nanocylinders: Up to Sixth-Generation Dendronized Polymers via Graft-Through Approach by ROMP.可调谐纳米圆柱体的构象：通过开环易位聚合（ROMP）的接枝法制备的高达第六代树枝状聚合物。
Macromolecules. 2019 May 14;52(9):3342-3350. doi: 10.1021/acs.macromol.9b00457. Epub 2019 Apr 23.
5
Efficient Conversion of Renewable Unsaturated Fatty Acid Methyl Esters by Cross-Metathesis with Eugenol.通过与丁香酚交叉复分解反应高效转化可再生不饱和脂肪酸甲酯
ACS Omega. 2018 Sep 12;3(9):11041-11049. doi: 10.1021/acsomega.8b01695. eCollection 2018 Sep 30.
6
Photosensitizer-Anchored 2D MOF Nanosheets as Highly Stable and Accessible Catalysts toward Artemisinin Production.光敏剂锚定的二维金属有机框架纳米片作为用于青蒿素生产的高度稳定且易于使用的催化剂
Adv Sci (Weinh). 2019 Apr 9;6(11):1802059. doi: 10.1002/advs.201802059. eCollection 2019 Jun 5.
7
An efficient synthesis of the guaiane sesquiterpene (-)-isoguaiene by domino metathesis.通过多米诺复分解反应高效合成愈创木烷倍半萜（-）-异愈创木烯。
Beilstein J Org Chem. 2019 Apr 9;15:858-862. doi: 10.3762/bjoc.15.83. eCollection 2019.
8
Catalytic living ring-opening metathesis polymerization with Grubbs' second- and third-generation catalysts.使用格拉布第二代和第三代催化剂的催化活性开环易位聚合反应。
Nat Chem. 2019 May;11(5):488-494. doi: 10.1038/s41557-019-0239-4. Epub 2019 Apr 8.
9
Isolation, Structure, and Total Synthesis of the Marine Macrolide Mangrolide D.海洋大环内酯 Mangrolide D 的分离、结构和全合成。
Org Lett. 2019 Apr 19;21(8):2957-2961. doi: 10.1021/acs.orglett.9b01126. Epub 2019 Apr 8.
10
Aqueous olefin metathesis: recent developments and applications.水相烯烃复分解反应：最新进展与应用
Beilstein J Org Chem. 2019 Feb 14;15:445-468. doi: 10.3762/bjoc.15.39. eCollection 2019.