三环吲哚生物碱 dilemmaones A 和 B 的合成
Synthesis of the tricyclic indole alkaloids, dilemmaones A and B.
作者信息
Lambson Katharine E, Dacko Christopher A, McNeill Jeffrey M, Akhmedov Novruz G, Söderberg Björn C G
机构信息
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506-6045, USA.
出版信息
Tetrahedron. 2019 Dec 6;75(49). doi: 10.1016/j.tet.2019.130714. Epub 2019 Oct 21.
Abstract
Dilemmaones A-C are naturally occurring tricyclic indole alkaloids possessing a unique hydroxymethylene or methoxymethylene substituent at the C2 position of the indole core and a C6-C7 fused cyclopentanone. Dilemmaone B has been prepared in 5 steps from 5-methylindan-1-one, and dilemmaone A has been prepared in 3 steps from a common precursor, 6-bromo-5-methyl-7-nitroindan-1-one. In both syntheses, key steps include a Kosugi-Migita-Stille cross coupling and a reductive cyclization using hydrogen gas and a transition metal catalyst.
摘要
困境化合物A - C是天然存在的三环吲哚生物碱，在吲哚核心的C2位置具有独特的羟基亚甲基或甲氧基取代基以及C6 - C7稠合环戊酮。困境化合物B由5 - 甲基茚满 - 1 - 酮经5步反应制备而成，困境化合物A由共同前体6 - 溴 - 5 - 甲基 - 7 - 硝基茚满 - 1 - 酮经3步反应制备而成。在这两种合成方法中，关键步骤包括小杉 - Migita - 施蒂勒交叉偶联反应以及使用氢气和过渡金属催化剂的还原环化反应。
相似文献
1
Synthesis of the tricyclic indole alkaloids, dilemmaones A and B.三环吲哚生物碱 dilemmaones A 和 B 的合成
Tetrahedron. 2019 Dec 6;75(49). doi: 10.1016/j.tet.2019.130714. Epub 2019 Oct 21.
2
A Divergent Enantioselective Total Synthesis of Post-Iboga Indole Alkaloids.一种 Iboga 吲哚生物碱的发散对映选择性全合成。
Angew Chem Int Ed Engl. 2020 Oct 12;59(42):18731-18740. doi: 10.1002/anie.202008242. Epub 2020 Aug 18.
3
Chemoselectivity in the Kosugi-Migita-Stille coupling of bromophenyl triflates and bromo-nitrophenyl triflates with (ethenyl)tributyltin.溴代苯基三氟甲磺酸酯和溴代硝基苯基三氟甲磺酸酯与（乙烯基）三丁基锡的小杉-沟田-斯蒂尔偶联反应中的化学选择性。
Tetrahedron. 2018 May 24;74(21):2547-2560. doi: 10.1016/j.tet.2018.02.051. Epub 2018 Apr 10.
4
Intramolecular dearomative oxidative coupling of indoles: a unified strategy for the total synthesis of indoline alkaloids.吲哚分子内去芳构化氧化偶联：吲哚啉生物碱全合成的统一策略。
Acc Chem Res. 2015 Mar 17;48(3):702-11. doi: 10.1021/ar5004303. Epub 2015 Feb 10.
5
Dilemmaones A-C, unusual indole alkaloids from a mixed collection of south african sponges.
J Nat Prod. 1998 May;61(5):699-701. doi: 10.1021/np970580m.
6
Formation of Cyclohepta[b]indole Scaffolds via Heck Cyclization: A Strategy for Structural Analogues of Ervatamine Group of Indole Alkaloid.通过Heck环化反应形成环庚并[b]吲哚骨架：一种制备吲哚生物碱埃文胺类结构类似物的策略。
J Org Chem. 2015 Jan 2;80(1):438-46. doi: 10.1021/jo502443a. Epub 2014 Dec 1.
7
Total synthesis of the tetracyclic indole alkaloid ht-13-B.四环吲哚生物碱ht-13-B的全合成
J Org Chem. 2015 May 1;80(9):4783-90. doi: 10.1021/acs.joc.5b00433. Epub 2015 Apr 10.
8
Synthetic Studies toward Dimeric Indole Alkaloids Based on Convergent Synthetic Strategy.基于汇聚式合成策略的二聚吲哚生物碱的合成研究
Chem Pharm Bull (Tokyo). 2020;68(2):117-128. doi: 10.1248/cpb.c19-00706.
9
Total Synthesis of (±)-Cis-Trikentrin B via Intermolecular 6,7-Indole Aryne Cycloaddition and Stille Cross-Coupling.通过分子间6,7-吲哚芳炔环加成和施蒂勒交叉偶联全合成（±）-顺式三肯曲林B
Tetrahedron Lett. 2013 Feb 20;54(8):913-917. doi: 10.1016/j.tetlet.2012.11.125.
10
Synthesis of the Core Tricyclic Ring Domain of (-)-Schulzeine B.（-）-舒尔采因B核心三环结构域的合成
J Org Chem. 2015 Aug 7;80(15):7790-6. doi: 10.1021/acs.joc.5b01173. Epub 2015 Jul 28.
引用本文的文献
1
Pd-Catalyzed Cross-Couplings: On the Importance of the Catalyst Quantity Descriptors, mol % and ppm.钯催化的交叉偶联反应：关于催化剂用量描述符mol%和ppm的重要性
Org Process Res Dev. 2022 Aug 19;26(8):2240-2269. doi: 10.1021/acs.oprd.2c00051. Epub 2022 Jul 11.
2
Isoindolin-1-ones from the stems of Nicotiana tabacum and their antiviral activities.从烟草茎中分离得到的异吲哚-1-酮及其抗病毒活性。
Arch Pharm Res. 2022 Aug;45(8):572-583. doi: 10.1007/s12272-022-01399-x. Epub 2022 Aug 20.
本文引用的文献
1
Six Trikentrin-like Cyclopentanoindoles from Trikentrion flabelliforme. Absolute Structural Assignment by NMR and ECD.三尖杉科三尖杉属植物中分离得到的 6 个三尖杉宁类似物。通过 NMR 和 ECD 对绝对结构进行鉴定。
J Org Chem. 2018 Feb 2;83(3):1278-1286. doi: 10.1021/acs.joc.7b02813. Epub 2018 Jan 23.
2
Syntheses of three naturally occurring polybrominated 3,3'-bi-1-indoles.三种天然存在的多溴代3,3'-联-1-吲哚的合成。
Tetrahedron Lett. 2017 Mar 15;58(11):1053-1056. doi: 10.1016/j.tetlet.2017.01.103. Epub 2017 Feb 3.
3
Application of a Palladium-Catalyzed C-H Functionalization/Indolization Method to Syntheses of cis-Trikentrin A and Herbindole B.钯催化的 C-H 功能化/吲哚化方法在 cis-三尖杉宁 A 和 Herbindole B 合成中的应用。
Angew Chem Int Ed Engl. 2016 Sep 19;55(39):11824-8. doi: 10.1002/anie.201605475. Epub 2016 Aug 29.
4
Diborane-Mediated Deoxygenation of o-Nitrostyrenes To Form Indoles.二硼烷介导的邻硝基苯乙烯脱氧反应生成吲哚。
Org Lett. 2016 Aug 19;18(16):4088-91. doi: 10.1021/acs.orglett.6b01934. Epub 2016 Aug 8.
5
A Practical, Multi-gram Synthesis of (±)-Herbindole A, (±)-Herbindole B, and (±)-Herbindole C from a Common Intermediate via 6,7-Indole Aryne Cycloaddition and Pd(0)-Catalyzed Cross-Coupling Reactions.通过6,7-吲哚芳炔环加成反应和钯（0）催化的交叉偶联反应，从一个共同中间体出发，实用的多克级合成（±）-赫宾多吲哚A、（±）-赫宾多吲哚B和（±）-赫宾多吲哚C。
Tetrahedron Lett. 2015 Jun 3;56(23):3507-3510. doi: 10.1016/j.tetlet.2015.02.064.
6
Aqueous Titanium Trichloride Promoted Reductive Cyclization of o-Nitrostyrenes to Indoles: Development and Application to the Synthesis of Rizatriptan and Aspidospermidine.三氯化钛水合物促进邻硝基苯乙烯的还原环化反应生成吲哚：在瑞扎曲坦和阿朴斯底醇的合成功效研究与应用。
Angew Chem Int Ed Engl. 2015 Sep 28;54(40):11809-12. doi: 10.1002/anie.201505713. Epub 2015 Aug 18.
7
Total synthesis of the tetracyclic indole alkaloid ht-13-B.四环吲哚生物碱ht-13-B的全合成
J Org Chem. 2015 May 1;80(9):4783-90. doi: 10.1021/acs.joc.5b00433. Epub 2015 Apr 10.
8
Eumelanin-inspired core derived from vanillin: a new building block for organic semiconductors.
Chem Commun (Camb). 2015 Feb 18;51(14):2957-9. doi: 10.1039/c4cc09011j.
9
Trikentramides A-D, indole alkaloids from the Australian sponge Trikentrion flabelliforme.三尖杉酰胺 A-D，澳大利亚海绵 Trikentrion flabelliforme 中的吲哚生物碱。
J Nat Prod. 2013 Nov 22;76(11):2100-5. doi: 10.1021/np400617h. Epub 2013 Nov 4.
10
Total synthesis of (+)-trans-trikentrin A.（+）-反式三可因 A 的全合成。
Chemistry. 2012 Dec 21;18(52):16890-901. doi: 10.1002/chem.201202413. Epub 2012 Nov 4.
Zotero 插件