Abstract
In order to test the hormonal activity of steroidal phosphonates on chicken embryos, several compounds have been prepared by addition of trimethyl phosphite (or dimethyl phosphonate) to 2-methylene-17β-hydroxy -4-androsten-3-one 10 and 2-methylene-17β-hydroxy-4-estren-3-one 3 . Structures of the compounds are discussed. Neat trimethyl phosphite can be added directly (without proton donor) to Δ 4-2-methylene-3-ketosteroids; possible mechanisms are discussed. The aromatization of 2-di-methylphosphonomethyl-17β-hydroxy-1, 4-androstadien-3-one 17-acetate 14 with 48% aqueous HBr gave exclusively (and unexpectedly) the “para” phenol: 2-dim.ethylphosphonomethyl-4 methyl-1, 3, 5(10) -estratriene-1,17β-diol 15 the structure of which was conclusively established by Nuclear Overhauser Effect (NOE) experiments. Biological assays on chicken embryos with 2-dimethylphosphonomethyl-3-hydroxy-l, 3, 5(10)-estratrien-17-one 9 and compound 15 were negative.
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