Coupling of low-order organocopper complexes with organoiron cations; synthesis of tamandron, a novel potentially antiandrogenic analogue of tamoxifen

Abstract

Low-order alkyl, aryl and vinyl organocopper complexes react efficiently with tricarbonyl(cyclohexadienylium)iron cations; the low-order vinylcopper complex derived from an (E)-1-bromo-1-(4-alkoxyphenyl)-2-phenylbut-1-ene couples the bulky vinyl group regioselectively, and with retention of the double-bond stereochemistry, to the encumbered C-5 methylsubstituted position of a tricarbonyl(2-alkoxy-5-methylcyclohexadienylium)iron cation, thereby forming a chiral quaternary carbon centre, and providing access to tamandron, a novel potentially antiandrogenic analogue of tamoxifen.