Synthesis of pentacyclic pyrrolo[3,4-a]carbazole-1,3(2H)-diones via an intermolecular Diels-Alder, intramolecular carbonyl-ene reaction strategy

被引：14

作者：

Abualnaja, Matokah ^{[1
]}

Waddell, Paul G. ^{[1
]}

Clegg, William ^{[1
]}

Hall, Michael J. ^{[1
]}

机构：

[1] Newcastle Univ, Sch Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

TETRAHEDRON | 2016年 / 72卷 / 38期

基金：

英国工程与自然科学研究理事会;

关键词：

Heterocycle synthesis; Carbazole; Diels-Alder cycloaddition; Ene reaction; ACTIVE CARBAZOLE ALKALOIDS; ASYMMETRIC-SYNTHESIS; FUNCTIONALIZED TETRAHYDROCARBAZOLES; ENANTIOSELECTIVE SYNTHESIS; BRONSTED ACID; DIASTEREOSELECTIVE SYNTHESIS; CASCADE REACTIONS; NATURAL-PRODUCTS; METAL-FREE; 3-VINYLINDOLES;

D O I：

10.1016/j.tet.2016.08.008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pentacyclic pyrrolo[3,4-a]carbazole-1,3(2H)-diones are accessed via two key synthetic steps, an intermolecular Diels-Alder (D-A) reaction between an N-protected 3-vinyl-1H-indole and N-methyl-maleimide, and a Lewis acid-catalysed intramolecular carbonyl-ene cyclisation reaction. Cyclopentyl-or cyclohexyl-containing scaffolds can be formed through variation in the length of the alkyl tether, whilst the observed stereospecificity of carbonyl-ene cyclisation supports a concerted mechanism. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：5798 / 5806

页数：9

共 67 条

[21] Synthesis of pyrido[2-3-b]indole derivatives via Diels-Alder reactions of 2-and 3-vinylpyrrolo[2,3-b]pyridines
Joseph, B
Da Costa, H
Mérour, JY
Léonce, S
[J]. TETRAHEDRON, 2000, 56 (20) : 3189 - 3196
[22] Palladium-Catalyzed α-Arylation of Enones in the Synthesis of 2-Alkenylindoles and Carbazoles
Kale, Ajit Prabhakar
Kumar, Gangam Srikanth
Mangadan, Arun Raj Kizhakkayil
Kapur, Manmohan
[J]. ORGANIC LETTERS, 2015, 17 (05) : 1324 - 1327
[23] Isolation and synthesis of biologically active carbazole alkaloids
Knölker, HJ
Reddy, KR
[J]. CHEMICAL REVIEWS, 2002, 102 (11) : 4303 - 4427
[24] Acid-free, organocatalytic acetalization
Kotke, M
Schreiner, PR
[J]. TETRAHEDRON, 2006, 62 (2-3) : 434 - 439
[25] Tandem Diels-Alder/ene reactions
Kraus, GA
Kim, J
[J]. ORGANIC LETTERS, 2004, 6 (18) : 3115 - 3117
[26] VINYLINDENES AND SOME HETEROANALOGUES IN THE DIELS-ALDER REACTION .8. 1-BENZYL-3-VINYLINDOLE AS A DIENE
LAMBERT, JD
PORTER, QN
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (07) : 1483 - 1490
[27] New carbanionic access to 3-vinylindoles and 3-vinylbenzofurans
Le Strat, F
Maddaluno, J
[J]. ORGANIC LETTERS, 2002, 4 (16) : 2791 - 2793
[28] Facile One-Pot Construction of Polycyclic Frameworks using a Synergistic Diels-Alder Reaction, Ene Reaction, and Allylation Reaction Strategy
Li, Dongzhen
Cao, Yang
Shi, An
Xi, Zhenfeng
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (02) : 392 - 395
[29] One-Pot Catalytic Asymmetric Synthesis of Tetrahydrocarbazoles
Liu, Qiong-Jie
Yan, Wen-Guang
Wang, Lijia
Zhang, X. Peter
Tang, Yong
[J]. ORGANIC LETTERS, 2015, 17 (16) : 4014 - 4017
[30] Multicatalytic Asymmetric Synthesis of Complex Tetrahydrocarbazoles via a Diels-Alder/Benzoin Reaction Sequence
Liu, Yankai
Nappi, Manuel
Escudero-Adan, Eduardo C.
Melchiorre, Paolo
[J]. ORGANIC LETTERS, 2012, 14 (05) : 1310 - 1313

← 1 2 3 4 5 6 7 →