Stereoselective synthesis of triarylethylenes via copper-palladium catalyzed decarboxylative cross-coupling: synthesis of (Z)-tamoxifen

被引：35

作者：

Cahiez, Gerard ^{[1
]}

Moyeux, Alban ^{[1
,2
]}

Poizat, Maeel ^{[2
]}

机构：

[1] CNRS, Chim ParisTech, Inst Rech Chim Paris, F-75005 Paris, France

[2] Univ Paris 13, Sorbonne Paris Cite, F-93017 Bobigny, France

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 64期

关键词：

TETRASUBSTITUTED OLEFINS; BREAST-CANCER; TAMOXIFEN; DERIVATIVES; ROUTE; ACIDS; ALKYNES; BOND;

D O I：

10.1039/c4cc03752a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first Cu/Pd-catalyzed decarboxylative cross-coupling of 3,3-diarylacrylic acids with aryl bromides is described. Triarylethylenes were obtained in high yields with excellent stereoselectivities. This methodology was successfully applied to the stereoselective synthesis of (Z)-tamoxifen.

引用

页码：8982 / 8984

页数：3

共 24 条

[1] Parallel synthesis of tamoxifen and derivatives on solid support via resin capture [J].

Brown, SD ;

Armstrong, RW .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7076-7077

[2] Copper-Catalyzed Decarboxylation of Aromatic Carboxylic Acids: En Route to Milder Reaction Conditions [J].

Cahiez, Gerard ;

Moyeux, Alban ;

Gager, Olivier ;

Poizat, Mael .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (04) :790-796

[3]

Clarke M, 1998, LANCET, V351, P1451

[4] CROSSED COUPLING OF FUNCTIONALIZED KETONES BY LOW VALENT TITANIUM (THE MCMURRY REACTION) - A NEW STEREOSELECTIVE SYNTHESIS OF TAMOXIFEN [J].

COE, PL ;

SCRIVEN, CE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (03) :475-477

[5] Tamoxifen for prevention of breast cancer: Report of the National Surgical Adjuvant Breast and Bowel Project P-1 study [J].

Fisher, B ;

Costantino, JP ;

Wickerham, DL ;

Redmond, CK ;

Kavanah, M ;

Cronin, WM ;

Vogel, V ;

Robidoux, A ;

Dimitrov, N ;

Atkins, J ;

Daly, M ;

Wieand, S ;

Tan-Chiu, E ;

Ford, L ;

Wolmark, N .

JOURNAL OF THE NATIONAL CANCER INSTITUTE, 1998, 90 (18) :1371-1388

[6] Stereocontrolled synthesis of tetrasubstituted olefins [J].

Flynn, Alison B. ;

Ogilvie, William W. .

CHEMICAL REVIEWS, 2007, 107 (11) :4698-4745

[7] Biaryl synthesis via Pd-catalyzed decarboxylative coupling of aromatic carboxylates with aryl halides [J].

Goossen, Lukas J. ;

Rodriguez, Nuria ;

Melzer, Bettina ;

Linder, Christophe ;

Deng, Guojun ;

Levy, Laura M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (15) :4824-4833

[8] Oxidative Heck Arylation for the Stereoselective Synthesis of Tetrasubstituted Olefins Using Nitroxides as Oxidants [J].

He, Zhiheng ;

Kirchberg, Sylvia ;

Froehlich, Roland ;

Studer, Armido .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (15) :3699-3702

[9] Tamoxifen: A most unlikely pioneering medicine [J].

Jordan, VC .

NATURE REVIEWS DRUG DISCOVERY, 2003, 2 (03) :205-213

[10] Antiestrogens and selective estrogen receptor modulators as multifunctional medicines. 1. Receptor interactions [J].

Jordan, VC .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (06) :883-908

← 1 2 3 →