Synthesis of 3-arylated indolines from dearomatization of indoles

被引：77
作者：
Denizot, Natacha
Tomakinian, Terry
Beaud, Rodolphe
Kouklovsky, Cyrille
Vincent, Guillaume [1 ]
机构：
[1] Univ Paris 11, F-91405 Orsay, France
来源：
TETRAHEDRON LETTERS | 2015年 / 56卷 / 30期
关键词：
Indole; Arylation; Dearomatization; Indoline; Natural products; CONCISE TOTAL-SYNTHESIS; NUCLEOPHILIC-SUBSTITUTION REACTION; N-ACETYL INDOLES; TRYPTOPHAN DERIVATIVES; DIAZONAMIDE-A; ARYLATION; CONSTRUCTION; CHEMISTRY; DIMERIZATION; CYCLIZATION;
D O I：
10.1016/j.tetlet.2015.05.078
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The introduction of aryl motifs at the C3-position of indole nuclei via dearomatization reactions has been the subject of intensive efforts in the last years and has culminated in several total syntheses of natural products. We provide in this digest Letter an overview of these recent advances including ours and we will highlight the fact that indoles could indeed act as nucleophiles but also as electrophiles and could be involved in radical reactions. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4413 / 4429
页数：17
相关论文
共 86 条
[1]   Enantioselective organocatalytic construction of pyrroloindolines by a cascade addition-cyclization strategy: Synthesis of (-)-flustramine B [J].
Austin, JF ;
Kim, SG ;
Sinz, CJ ;
Xiao, WJ ;
MacMillan, DWC .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (15) :5482-5487
[2]   Electrophilicity: the "dark-side" of indole chemistry [J].
Bandini, Marco .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (32) :5206-5212
[3]   THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS .7. THE POSSIBLE ROLE OF RADICAL MECHANISMS IN THE PHENYLATION PROCESS FOR BISMUTH(V), AND RELATED LEAD(IV), IODINE(III), AND ANTIMONY(V) REAGENTS [J].
BARTON, DHR ;
FINET, JP ;
GIANNOTTI, C ;
HALLEY, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (01) :241-249
[4]   The Quest for an Oxidative Coupling of Phenols and Indoles towards Benzofuroindolines: A Two-Stage Approach [J].
Beaud, Rodolphe ;
Tomakinian, Terry ;
Denizot, Natacha ;
Pouilhes, Annie ;
Kouklovsky, Cyrille ;
Vincent, Guillaume .
SYNLETT, 2015, 26 (04) :432-440
[5]   Regioselective Hydroarylation Reactions of C3 Electrophilic N-Acetylindoles Activated by FeCl3: An Entry to 3-(Hetero)arylindolines [J].
Beaud, Rodolphe ;
Guillot, Regis ;
Kouklovsky, Cyrille ;
Vincent, Guillaume .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (24) :7492-7500
[6]   FeCl3-Mediated Friedel-Crafts Hydroarylation with Electrophilic N-Acetyl Indoles for the Synthesis of Benzofuroindolines [J].
Beaud, Rodolphe ;
Guillot, Regis ;
Kouklovsky, Cyrille ;
Vincent, Guillaume .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (50) :12546-12550
[7]   Remarkably reactive dihydroindoloindoles via palladium-catalysed dearomatisation [J].
Bedford, Robin B. ;
Fey, Natalie ;
Haddow, Mairi F. ;
Sankey, Rosalind F. .
CHEMICAL COMMUNICATIONS, 2011, 47 (12) :3649-3651
[8]   An Interrupted Fischer Indolization Approach toward Fused Indoline-Containing Natural Products [J].
Boal, Ben W. ;
Schammel, Alex W. ;
Garg, Neil K. .
ORGANIC LETTERS, 2009, 11 (15) :3458-3461
[9]   Concise total synthesis of (+)-gliocladins B and C [J].
Boyer, Nicolas ;
Movassaghi, Mohammad .
CHEMICAL SCIENCE, 2012, 3 (06) :1798-1803
[10]   A concise and flexible total synthesis of (-)-diazonamide A [J].
Burgett, AWG ;
Li, QY ;
Wei, Q ;
Harran, PG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (40) :4961-4966
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