title: Simple and efficient production of (Z)-4-hydroxytamoxifen, a potent estrogen receptor modulator.
abstract: 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.
authors: Division of Molecular Medicine, The Beckman Research Institute, The City of Hope National Medical Center, Duarte, California 91010, USA.
authors: Donna D
authors: DD
authors: Yu
authors: Barry M
authors: BM
authors: Forman
mesh_terms: D001667:Binding, Competitive; D003460:Crystallization; D004958:Estradiol / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D020845:Selective Estrogen Receptor Modulators / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013629:Tamoxifen / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D020845:Selective Estrogen Receptor Modulators; D013629:Tamoxifen; C016601:afimoxifene; D004958:Estradiol