potassium tert-butylate in dimethyl sulfoxide T=40°C; 15 h;

potassium tert-butylate in dimethyl sulfoxide T=40°C; 38 h;

1: 92 percent / potassium hydroxide / benzene; methanol / 3 h / Heating 2: 86 percent / potassium t-butoxide / dimethylsulfoxide / 15 h / 40 °C View Scheme

2: 92 percent / potassium hydroxide / benzene; methanol / 3 h / Heating 3: 86 percent / potassium t-butoxide / dimethylsulfoxide / 15 h / 40 °C View Scheme

1: 92 percent / toluene-p-sulphonic acid / acetone / 19 h / 15 °C 2: 4M NaOH, 30percent H2O2 / 2-methyl-propan-2-ol / 3 h / 15 - 20 °C 3: 49 percent / 4-dimethylaminopyridine, triethylamine / CH2Cl2 / 15 h / Ambient temperature 6: 100 percent / H2 / platinum (10percent) on carbon / ethyl acetate / 8.5 h / Ambient temperature 7: 95 percent / toluene-p-sulphonic acid / acetone; H2O / 3 h / Heating 8: 100 percent / pyridine / 48 h 9: BH3-THF / tetrahydrofuran / 0 deg C, 10 min, RT, 6 h 10: 88 percent / 5percent KOH / methanol / 48 h / Ambient temperature 11: 65 percent / pyridinium dichromate / CH2Cl2 / 60 h 12: 20 mg / K2CO3, hydrazine hydrate 85percent, triethylene glycol / 150 deg C, 1 h, 220 deg C, 5.5 h View Scheme

1: 17,17-ethylenedioxy-3β-hydroxyandrosta-5,15-diene With toluene-4-sulfonic acid in water; acetone 18 h; Inert atmosphere; 2: acetic anhydride With pyridine; 4-(N,N-dimethlyamino)pyridine in dichloromethane 24 h; Inert atmosphere;