Rhodium- and Platinum-Catalyzed [4+3] Cycloaddition with Concomitant Indole Annulation: Synthesis of Cyclohepta[b]indoles

被引：89

作者：

Shu, Dongxu ^{[1
,2
]}

Song, Wangze ^{[1
]}

Li, Xiaoxun ^{[1
]}

Tang, Weiping ^{[1
]}

机构：

[1] Univ Wisconsin, Sch Pharm, Madison, WI 53705 USA

[2] Univ Wisconsin, Dept Chem, Madison, WI 53705 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 11期

关键词：

cycloaddition; heterocycles; homogeneous catalysis; transition metals; CYCLOPROPANATION COPE REARRANGEMENT; FISCHER CARBENE COMPLEXES; ACTINOPHYLLIC ACID; DIASTEREOSELECTIVE SYNTHESIS; PROPARGYLIC CARBOXYLATES; 7-MEMBERED RINGS; GOLD CATALYSIS; DERIVATIVES; MIGRATION; ERVITSINE;

D O I：

10.1002/anie.201209266

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Various substituted cyclohepta[b]indoles were prepared from propargylic ethers and dienes by a tandem indole annulation/[4+3] cycloaddition (see scheme; Boc=tert-butoxycarbonyl). Both acyclic and cyclic dienes participated in the [4+3] cycloaddition to afford tri- and tetracyclic products, respectively. Electron-deficient phosphine or phosphite ligands facilitated the tandem reaction. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：3237 / 3240

页数：4

共 60 条

[1] Generation of α,β-Unsaturated Platinum Carbenes from Homopropargylic Alcohols: Rearrangements to Polysubstituted Furans [J].

Allegretti, Paul A. ;

Ferreira, Eric M. .

ORGANIC LETTERS, 2011, 13 (21) :5924-5927

[2] A Synthetic Approach to Ervatamine-Silicine Alkaloids. Enantioselective Total Synthesis of (-)-16-Episilicine [J].

Amat, Mercedes ;

Llor, Nuria ;

Checa, Begona ;

Molins, Elies ;

Bosch, Joan .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (01) :178-189

[3]

ANDRIANTSIFERANA M, 1977, TETRAHEDRON LETT, P2587

[4]

[Anonymous], 2012, ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANGE.201205238

[5] Diastereoselective synthesis of three-, five-, six-, and seven-membered rings from Fischer carbene complexes and 4-unsubstituted 1-amino-1,3-dienes [J].

Aznar, Fernando ;

Fananas-Mastral, Martin ;

Alonso, Jorge ;

Fananas, Francisco J. .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (01) :325-332

[6] N-Benzyl-indolo carboxylic acids: Design and synthesis of potent and selective adipocyte fatty-acid binding protein (A-FABP) inhibitors [J].

Barf, Tjeerd ;

Lehmann, Fredrik ;

Hammer, Kristin ;

Haile, Saba ;

Axen, Eva ;

Medina, Carmen ;

Uppenberg, Jonas ;

Svensson, Stefan ;

Rondahl, Lena ;

Lundbaeck, Thomas .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (06) :1745-1748

[7] Diastereoselective synthesis of five- and seven-membered rings by [2+2+1], [3+2], [3+2+2], and [4+3] carbocyclization reactions of β-substituted (alkenyl)(methoxy)carbene complexes with methyl ketone lithium enolates [J].

Barluenga, J ;

Alonso, J ;

Fañanás, FJ .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (17) :4995-5006

[8]

Barluenga J, 2000, ANGEW CHEM INT EDIT, V39, P2460

[9] STEREOSELECTIVE SYNTHESIS OF 7-MEMBERED CARBOCYCLES FROM 2-AMINO-1,3-BUTADIENES AND VINYL CHROMIUM FISCHER-TYPE CARBENES [J].

BARLUENGA, J ;

AZNAR, F ;

MARTIN, A ;

VAZQUEZ, JT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (37) :9419-9426

[10] Formal [4+3], [4+2], [4+1] and [2+1] cycloadditions and acid-base reaction of 2-methyl-1,3-dimorpholino-1,3-butadiene with Fischer carbene complexes [J].

Barluenga, J ;

Aznar, F ;

Fernandez, M .

CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (10) :1629-1637

← 1 2 3 4 5 6 →