trans-Stilbene as a Starting Material for the Synthesis of Tamoxifen Based on Palladium-Catalyzed Cross-Coupling Reactions

被引：14

作者：

Nunes, Carolina M. ^{[1
]}

Limberger, Jones ^{[1
]}

Poersch, Silvia ^{[1
]}

Seferin, Marcus ^{[1
]}

Monteiro, Adriano L. ^{[1
]}

机构：

[1] Univ Fed Rio Grande do Sul, Inst Quim, Lab Mol Catalysis, BR-9500 Porto Alegre, RS, Brazil

来源：

SYNTHESIS-STUTTGART | 2009年 / 16期

关键词：

tamoxifen; cross-coupling; stilbene; substituted olefins; palladium; TETRASUBSTITUTED OLEFINS; STEREOSELECTIVE-SYNTHESIS; ARYLBORONIC ACIDS; ARYL HALIDES; (Z)-TAMOXIFEN; DERIVATIVES; ALKYNES; ALKENES; CARBOMETALATION; CARBOZINCATION;

D O I：

10.1055/s-0029-1217600

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(Z)-Tamoxifen was synthesized from a simple olefin (trans-stilbene) in 5 steps and 40% overall yield (Z/E = 74:26). The phenyl substituted group (4-Me2NCH2CH2OC6H4) was attached by a bromination-dehydrobromination-Suzuki reaction sequence. Subsequently, the ethyl group was attached to the triarylated olefin by a bromination-Negishi reaction sequence. Both the Suzuki and Negishi cross-coupling processes are stereospecific, and the stereoselectivity depends only on the bromination-dehydrobromination reactions. (Z)-Tamoxifen was also obtained from trans-stilbene in only 3 steps by using Heck reaction-bromination-Negishi reaction sequence in 57% overall yield (Z/E = 65:35).

引用

页码：2761 / 2765

页数：5

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