Simple and Efficient Production of (Z)-4-Hydroxytamoxifen, a Potent Estrogen Receptor Modulator

• Published in: Journal of organic chemistry Vol. 68; no. 24; pp. 9489 - 9491
• Main Authors: Yu, Donna D, Forman, Barry M
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 28.11.2003; Amer Chemical Soc
• Subjects: Binding, Competitive; Chemistry; Chemistry, Organic; Crystallization; Estradiol - chemistry; Exact sciences and technology; Models, Chemical; Molecular Structure; Noncondensed benzenic compounds; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Selective Estrogen Receptor Modulators - chemical synthesis; Selective Estrogen Receptor Modulators - chemistry; Stereoisomerism; Structure-Activity Relationship; Tamoxifen - analogs & derivatives; Tamoxifen - chemical synthesis; Tamoxifen - chemistry; ANTIESTROGENS; SERMS; TAMOXIFEN; ISOMERIZATION; ISOMERS; DIETHYLSTILBESTROL; BINDING; Estrogen receptor; Modulator; Metabolite; Crystallization; Breast; Aromatic compound; Selectivity; Malignant tumor; Chemical synthesis; Ethylenic compound; Tamoxifene; Chemical coupling
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo035164n

A McMurry coupling reaction and selective crystallization were used to develop a simple and efficient two-step synthesis of (Z)-4-hydroxytamoxifen (2a). This compound is an active metabolite of tamoxifen, a selective estrogen receptor (ER) modulator widely used to treat breast cancer. The synthesis employed 1,1-bis(4-hydroxyphenyl)-2-phenylbut-1-ene (1) as a useful building block.