Tandem Heck-Suzuki-Miyaura reaction: Application to the synthesis of constrained analogues of combretastatin A-4

被引：38

作者：

Arthuis, Martin

Pontikis, Renee

Florent, Jean-Claude

机构：

[1] Ctr Rech, Inst Curie, F-75248 Paris, France

[2] CNRS, UMR 176, F-75248 Paris, France

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 36期

关键词：

combretastatin A4; oxindole; domino reaction; palladium catalysis;

D O I：

10.1016/j.tetlet.2007.06.129

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of compounds related to combretastatin A-4 has been synthesized by a tandem Heck-carbocyclization/Suzuki coupling process. From various alkynamides and 3,4,5-trimethoxyphenyl boronic acid or the corresponding styryl derivative, (E)-3-arylmethyleneoxindoles (type I) and (EE)-3-alkylideneoxindoles (type II) were efficiently obtained in a stereoselective manner. Factors influencing yield and stereoselectivity are detailed. (C) 2007 Elsevier Ltd. All rights reserved.

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页码：6397 / 6400

页数：4

相关论文

共 21 条

[1] Antitumor activity of substituted E-3-(3,4,5-trimethoxybenzylidene)-1,3-dihydroindol-2-ones [J].

Andreani, Aldo ;

Burnelli, Silvia ;

Granaiola, Massimiliano ;

Leoni, Alberto ;

Locatelli, Alessandra ;

Morigi, Rita ;

Rambaldi, Mirella ;

Varoli, Lucilla ;

Kunkel, Mark W. .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (23) :6922-6924

[2] The synthesis of 3-methyleneindol-2(3H)-ones related to mitomycins via 5-exo-dig aryl radical cyclisation [J].

Brunton, SA ;

Jones, K .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (05) :763-768

[3] REGIOSPECIFIC PALLADIUM CATALYZED TANDEM CYCLISATION-ANION CAPTURE PROCESSES - STEREOSPECIFIC GROUP TRANSFER FROM ORGANOZINC AND ORGANOBORON REAGENTS [J].

BURNS, B ;

GRIGG, R ;

SRIDHARAN, V ;

STEVENSON, P ;

SUKIRTHALINGAM, S ;

WORAKUN, T .

TETRAHEDRON LETTERS, 1989, 30 (09) :1135-1138

[4] A tandem Heck-carbocyclization/Suzuki-coupling approach to the stereoselective syntheses of asymmetric 3,3-(diarylmethylene)indolinones [J].

Cheung, WS ;

Patch, RJ ;

Player, MR .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (09) :3741-3744

[5] Heck-Suzuki-Miyaura domino reactions involving ynamides.: An efficient access to 3-(Arylmethylene)isoindolinones [J].

Couty, S ;

Liégault, B ;

Meyer, C ;

Cossy, J .

ORGANIC LETTERS, 2004, 6 (15) :2511-2514

[6] Potent antimitotic and cell growth inhibitory properties of substituted chalcones [J].

Ducki, S ;

Forrest, R ;

Hadfield, JA ;

Kendall, A ;

Lawrence, NJ ;

McGown, AT ;

Rennison, D .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (09) :1051-1056

[7] Synthesis and evaluation of double bond substituted combretastatins [J].

Hadfield, JA ;

Gaukroger, K ;

Hirst, N ;

Weston, AP ;

Lawrence, NJ ;

McGown, AT .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2005, 40 (06) :529-541

[8]

HSEIH HP, 2005, CURR PHARM, P1655

[9] Synthesis and biological evaluation of vinylogous combretastatin A-4 derivatives [J].

Kaffy, J ;

Pontikis, RE ;

Florent, JC ;

Monneret, C .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (14) :2657-2660

[10] Vascular disrupting agents [J].

Lippert, John W., III .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (02) :605-615