一种通过钯催化多米诺反应合成二聚体白藜芦醇天然产物的方法。
An approach to the synthesis of dimeric resveratrol natural products via a palladium-catalyzed domino reaction.
作者信息
Jeffrey Jenna L, Sarpong Richmond
机构信息
Department of Chemistry, University of California, Berkeley, California 94720.
出版信息
Tetrahedron Lett. 2009 Apr 29;50(17):1969-1972. doi: 10.1016/j.tetlet.2009.02.067.
Abstract
A route for the rapid assembly of the carbon framework of several resveratrol natural products is presented. A palladium-catalyzed domino reaction of bromostilbene derivative 6 and tolane 7, involving two sequential Heck coupling reactions, provides access to the benzofulvene-based core of various resveratrol-derived natural products. The carbon skeleton of pallidol and its congeners is achieved by a Lewis acid-induced Nazarov-type oxidative cyclization of 9.
摘要
本文介绍了一种快速组装几种白藜芦醇天然产物碳骨架的方法。溴代芪衍生物6与苯乙炔7的钯催化多米诺反应，涉及两个连续的Heck偶联反应，可用于构建各种白藜芦醇衍生天然产物的基于苯并富烯的核心结构。通过9的路易斯酸诱导的Nazarov型氧化环化反应可得到苍白霉素及其同系物的碳骨架。
相似文献
1
An approach to the synthesis of dimeric resveratrol natural products via a palladium-catalyzed domino reaction.一种通过钯催化多米诺反应合成二聚体白藜芦醇天然产物的方法。
Tetrahedron Lett. 2009 Apr 29;50(17):1969-1972. doi: 10.1016/j.tetlet.2009.02.067.
2
Total synthesis of resveratrol-based natural products using a palladium-catalyzed decarboxylative arylation and an oxidative Heck reaction.基于钯催化脱羧芳基化和氧化 Heck 反应的白藜芦醇类天然产物的全合成。
Angew Chem Int Ed Engl. 2014 Feb 24;53(9):2473-6. doi: 10.1002/anie.201310676. Epub 2014 Feb 5.
3
Domino Pd-catalyzed Heck cyclization and bismuth-catalyzed hydroamination: formal synthesis of elacomine and isoelacomine.多马钯催化的 Heck 环化和铋催化的氢胺化：埃拉考胺和异埃拉考胺的形式合成。
Chemistry. 2011 Jan 10;17(2):626-33. doi: 10.1002/chem.201002287. Epub 2010 Nov 16.
4
Enantioselective Pd-catalyzed dearomative reductive Heck and domino Heck-Suzuki reactions of 2-CF-indoles.对映选择性 Pd 催化的去芳构化还原 Heck 和 Heck-Suzuki 串联反应的 2-CF-吲哚。
Chem Commun (Camb). 2022 May 24;58(42):6200-6203. doi: 10.1039/d2cc01435a.
5
Aromatic π-Components for Enantioselective Heck Reactions and Heck/Anion-Capture Domino Sequences.用于对映选择性 Heck 反应和 Heck/阴离子捕获多米诺序列的芳族π-组分。
Acc Chem Res. 2022 Mar 1;55(5):734-745. doi: 10.1021/acs.accounts.1c00781. Epub 2022 Feb 4.
6
Recent Advances in the Synthesis of 3,n-Fused Tricyclic Indole Skeletons via Palladium-Catalyzed Domino Reactions.钯催化的多米诺反应在 3,n-稠合三环吲哚骨架合成中的最新进展。
Molecules. 2023 Feb 8;28(4):1647. doi: 10.3390/molecules28041647.
7
Palladium-Catalyzed Heck-type Domino Cyclization and Carboxylation to Synthesize Carboxylic Acids by Utilizing Chloroform as the Carbon Monoxide Source.钯催化的Heck型多米诺环化反应及羧基化反应：以氯仿作为一氧化碳源合成羧酸
J Org Chem. 2015 Aug 7;80(15):7547-54. doi: 10.1021/acs.joc.5b01126. Epub 2015 Jul 10.
8
Total Synthesis of Cyclopiamide A Using Palladium-Catalyzed Domino Cyclization.钯催化的多米诺环化反应全合成环巴胺 A
Molecules. 2020 Oct 23;25(21):4903. doi: 10.3390/molecules25214903.
9
An Approach toward 17-Arylsubstituted Marginatafuran-Type Isospongian Diterpenoids via a Palladium-Catalyzed Heck-Suzuki Cascade Reaction of 16-Bromolambertianic Acid.一种通过钯催化 Heck-Suzuki 级联反应合成 17-芳基取代的 Marginatafuran 型异海绵二萜的方法，涉及 16-溴 Lambertianic 酸。
Molecules. 2022 Apr 20;27(9):2643. doi: 10.3390/molecules27092643.
10
Efficient synthesis of the structural core of tetracyclines by a palladium-catalyzed domino Tsuji-Trost-Heck-Mizoroki reaction.通过钯催化的多米诺Tsuji-Trost-Heck-Mizoroki反应高效合成四环素的结构核心。
Chemistry. 2008;14(8):2527-35. doi: 10.1002/chem.200701676.
引用本文的文献
1
An organometallic analogue of combretastatin A-4 and its apoptosis-inducing effects on lymphoma, leukemia and other tumor cells .一种康普他汀A - 4的有机金属类似物及其对淋巴瘤、白血病和其他肿瘤细胞的凋亡诱导作用。
RSC Med Chem. 2022 Jun 30;13(9):1044-1051. doi: 10.1039/d2md00144f. eCollection 2022 Sep 21.
2
Electrochemically Mediated Oxidation of Sensitive Propargylic Benzylic Alcohols.敏感炔丙基苄醇的电化学介导氧化
Org Lett. 2022 Feb 25;24(7):1423-1428. doi: 10.1021/acs.orglett.1c03860. Epub 2022 Feb 11.
3
Chemistry and Biology of Resveratrol-Derived Natural Products.白藜芦醇衍生天然产物的化学与生物学
Chem Rev. 2015 Sep 9;115(17):8976-9027. doi: 10.1021/cr500689b. Epub 2015 Apr 2.
4
A scalable biomimetic synthesis of resveratrol dimers and systematic evaluation of their antioxidant activities.白藜芦醇二聚体的可扩展仿生合成及其抗氧化活性的系统评价。
Angew Chem Int Ed Engl. 2015 Mar 16;54(12):3754-7. doi: 10.1002/anie.201409773. Epub 2015 Feb 4.
5
Total syntheses of hopeanol and hopeahainol A empowered by a chiral Brønsted acid induced pinacol rearrangement.由手性布朗斯特酸诱导的频哪醇重排实现的霍普醇和霍普海醇A的全合成。
Angew Chem Int Ed Engl. 2012 Apr 23;51(17):4080-4. doi: 10.1002/anie.201107730. Epub 2012 Mar 16.
6
Structural revision and total synthesis of caraphenol B and C.Caraphenol B 和 C 的结构修订和全合成。
Org Lett. 2011 Oct 21;13(20):5524-7. doi: 10.1021/ol2022406. Epub 2011 Sep 26.
7
Concise synthesis of pauciflorol F using a Larock annulation.使用 Larock 环化反应简洁合成少瓣獐牙菜苦苷 F
Org Lett. 2009 Dec 3;11(23):5450-3. doi: 10.1021/ol902141z.
本文引用的文献
1
Total synthesis of diverse carbogenic complexity within the resveratrol class from a common building block.从一个共同的构建模块出发，对白藜芦醇类化合物中多样的碳源复杂性进行全合成。
J Am Chem Soc. 2009 Feb 11;131(5):1753-65. doi: 10.1021/ja806183r.
2
Total synthesis of resveratrol-based natural products: a chemoselective solution.基于白藜芦醇的天然产物的全合成：一种化学选择性解决方案。
Angew Chem Int Ed Engl. 2007;46(43):8186-91. doi: 10.1002/anie.200703333.
3
Total synthesis of (+/-)-quadrangularin A.（±）-四角豆素A的全合成
Angew Chem Int Ed Engl. 2006 Nov 20;45(45):7609-11. doi: 10.1002/anie.200603097.
4
Synthesis and biological evaluation of boronic acid containing cis-stilbenes as apoptotic tubulin polymerization inhibitors.含硼酸的顺式二苯乙烯作为凋亡性微管蛋白聚合抑制剂的合成及生物学评价
ChemMedChem. 2006 Jul;1(7):729-40. doi: 10.1002/cmdc.200600068.
5
Resveratrol prolongs lifespan and retards the onset of age-related markers in a short-lived vertebrate.白藜芦醇可延长一种短寿命脊椎动物的寿命，并延缓与衰老相关指标的出现。
Curr Biol. 2006 Feb 7;16(3):296-300. doi: 10.1016/j.cub.2005.12.038.
6
Cytotoxic properties of oligostilbenoids from the tree barks of Hopea dryobalanoides.羯布罗香树皮中低聚芪类化合物的细胞毒性特性
Z Naturforsch C J Biosci. 2005 Sep-Oct;60(9-10):723-7. doi: 10.1515/znc-2005-9-1011.
7
Phloroglucinol derivatives from Mallotus pallidus.来自白背叶的间苯三酚衍生物。
Phytochemistry. 2004 Sep;65(18):2589-94. doi: 10.1016/j.phytochem.2004.08.003.
8
Three new resveratrol oligomers from the stem bark of Vatica pauciflora.从少花青梅茎皮中分离得到的三种新白藜芦醇低聚物。
J Nat Prod. 2004 Jun;67(6):932-7. doi: 10.1021/np030236r.
9
Domino Reactions in Organic Synthesis.有机合成中的多米诺反应。
Chem Rev. 1996 Feb 1;96(1):115-136. doi: 10.1021/cr950027e.
10
Oligostilbenoids in stem bark of Vatica rassak.青梅茎皮中的低聚芪类化合物。
Phytochemistry. 2000 May;54(1):63-9. doi: 10.1016/s0031-9422(00)00026-1.
Zotero 插件