1: estra-1,3,5(10)-triene-3,17β-diol 3,17β-bis(methoxymethoxy) ether With sec.-butyllithium in tetrahydrofuran; cyclohexane T=-78°C; 2.5 h; 2: N,N-dimethyl-formamide in tetrahydrofuran; cyclohexane T=-78 - 23°C; 3 h;

1: 97 percent / diisopropylethylamine / tetrahydrofuran / Heating 2: 1.) s-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C to RT, overnight View Scheme

1: formaldehyd; [125I]-Estradiol With triethylamine; magnesium chloride in tetrahydrofuran Reflux; 2: With lithium hydroxide hydrate in methanol 3: chloromethyl methyl ether With N-ethyl-N,N-diisopropylamine in tetrahydrofuran Heating; regioselective reaction;

potassium hydride in tetrahydrofuran Etherification;

1: m-chloroperbenzoic acid; Na2HPO4 2: H2O 3: K2CO3 / dimethylformamide / 20 °C 4: trifluoroacetic acid / CH2Cl2; dimethylformamide / 0.17 h / 80 °C View Scheme

1: With sodium hydrogen orthophosphate dihydrate; 3-chloro-benzenecarboperoxoic acid in dichloromethane T=20°C; Dakin oxidation; 24 h; 2: With sodium hydroxide in methanol T=20°C; 2 h;