Short-step synthesis of tamoxifen and its derivatives via the three-component coupling reaction and migration of the double bond

被引：24

作者：

Shiina, I ^{[1
]}

Suzuki, M ^{[1
]}

Yokoyama, K ^{[1
]}

机构：

[1] Sci Univ Tokyo, Fac Sci, Dept Appl Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 05期

关键词：

D O I：

10.1016/j.tetlet.2003.11.119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The anti-tumor agent, tamoxifen, is easily synthesized by the successive allylation of benzaldehyde and the Friedel-Crafts alkylation reaction of anisole with the intermediary homoallyl silyl ethers, followed by the migration of the double bond to form the desired tetra-substituted ethylenes. Several derivatives of tamoxifen are also produced according to a similar synthetic strategy. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：965 / 967

页数：3

共 26 条

[21]

SHINOZAKI F, 1995, Patent No. 9511879

[22] New nickel-catalyzed carbozincation of alkynes: A short synthesis of (Z)-tamoxifen [J].

Studemann, T ;

Knochel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :93-95

[23] A nickel-catalyzed carbozincation of aryl-substituted alkynes [J].

Stüdemann, T ;

Ibrahim-Ouali, M ;

Knochel, P .

TETRAHEDRON, 1998, 54 (07) :1299-1316

[24] (Z)-tamoxifen and tetrasubstituted alkenes and dienes via a regio- and stereospecific three-component magnesium carbometalation palladium(0) cross-coupling strategy [J].

Tessier, PE ;

Penwell, AJ ;

Souza, FES ;

Fallis, AG .

ORGANIC LETTERS, 2003, 5 (17) :2989-2992

[25]

WHITE DA, 1984, Patent No. 127128

[26] DIETHYLSTILBESTROL CIS-TRANS ISOMERIZATION AND ESTROGEN ACTIVITY OF DIETHYLSTILBESTROL ISOMERS [J].

WINKLER, VW ;

NYMAN, MA ;

EGAN, RS .

STEROIDS, 1971, 17 (02) :197-&

← 1 2 3 →