1: 77.5 percent / acetic acid; H2O / 1 h / 90 °C 2: 75 percent / H2 / 10percent palladium-charcoal / ethanol / 1.5 h / Ambient temperature 3: dimethylformamide / 0.5 h / Heating 4: hydriodic acid, NaOAc, O2 / acetic acid / 20 h 5: aq. 2N KOH / tetrahydrofuran; H2O / 24 h / 20 °C View Scheme

1: 77.5 percent / acetic acid; H2O / 1 h / 90 °C 2: 75 percent / H2 / 10percent palladium-charcoal / ethanol / 1.5 h / Ambient temperature 3: dimethylformamide / 0.5 h / Heating 4: hydriodic acid, NaOAc, O2 / acetic acid / 20 h 5: aq. 2N KOH / tetrahydrofuran; H2O / 24 h / 20 °C 6: 2N aq. KOH, 3percent sodium amalgam / 0.08 h / dark 7: 2.) H2SO4 / 1.) beef-liver mitochondria, 0.2M Tris-HCl buffer (pH 7.8), 38 deg C, 22 h, 2.) 25 deg C View Scheme

1: 81 percent / p-toluene sulfonic acid hydrate / acetic acid / 4 h / 45 °C 2: 92 percent / H2, triethylamine / 10percent palladised charcoal / tetrahydrofuran / 760 Torr / Ambient temperature 3: 85 percent / 1) toluene p-sulfonic acid hydrate; 2) HBr / CH2Cl2; methanol / 16 h 4: 42 percent / trifluoroacetic acid / 0.25 h / Ambient temperature 5: 54 percent / 3percent aqeous sodium hydroxide / pyridine / 2.5 h / Heating View Scheme