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
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
收藏
页码:965 / 967
页数:3
相关论文
共 26 条
[1]  
ALHASSAN MI, 1987, SYNTHESIS-STUTTGART, P816
[2]   SYNTHESIS OF CIS-TAMOXIFEN AND TRANS-TAMOXIFEN [J].
ALHASSAN, MI .
SYNTHETIC COMMUNICATIONS, 1987, 17 (10) :1247-1251
[3]   BASE-CATALYZED ISOMERIZATION OF VINYLCYCLOHEXENE AND DIPENTENE [J].
BANK, S ;
ROWE, CA ;
SCHRIESH.A ;
NASLUND, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) :221-&
[4]   PREPARATION AND IDENTIFICATION OF CIS AND TRANS ISOMERS OF SUBSTITUTED TRIARYLETHYLENE [J].
BEDFORD, GR ;
RICHARDSON, DN .
NATURE, 1966, 212 (5063) :733-+
[5]   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
[6]   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
[7]   New highly stereoselective synthesis of (Z)-4-Hydroxytamoxifen and (Z)-4-hydroxytoremifene via McMurry reaction [J].
Gauthier, S ;
Mailhot, J ;
Labrie, F .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3890-3893
[8]   New highly stereoselective synthesis of (E)-droloxifene via selective protection of 3,4′-dihydroxybenzophenone and McMurry reaction [J].
Gauthier, S ;
Sancéau, JY ;
Mailhot, J ;
Caron, B ;
Cloutier, J .
TETRAHEDRON, 2000, 56 (05) :703-709
[9]   CONTRASTING ENDOCRINE ACTIVITIES OF CIS AND TRANS ISOMERS IN A SERIES OF SUBSTITUTED TRIPHENYLETHYLENES [J].
HARPER, MJK ;
WALPOLE, AL .
NATURE, 1966, 212 (5057) :87-&
[10]  
HARPOR MJK, 1965, Patent No. 1013907