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Ring-substituted 1,2-dialkylated 1,2-bis(hydroxyphenyl)ethanes. 2. Synthesis and estrogen receptor binding affinity of 4,4'-, 5,5'-, and 6,6'-disubstituted metahexestrols

Hartmann, Rolf W. ; Heindl, Aledander ; Schönenberger, Helmut



Abstract

Sym. 4,4'-, 5,5'-, and 6,6'-disubstituted derivs. of the mammary tumor-inhibiting antiestrogen metahexestrol (meso-I, R = H) (II) were prepd. Reductive coupling of EtCOC6H4R with TiCl4/Zn followed by hydrogenation, or reductive coupling of EtCH(OH)C6H4R with TiCl3/LiAlH4, and sepn. of the diastereomers, or substitution reaction of II gave meso-I (R = Me, MeOCH2, EtOCH2, HOCH2, halo, NO2, OH, ...

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