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

1: 75 percent / H2 / 10percent palladium-charcoal / ethanol / 1.5 h / Ambient temperature 2: dimethylformamide / 0.5 h / Heating 3: hydriodic acid, NaOAc, O2 / acetic acid / 20 h 4: aq. 2N KOH / tetrahydrofuran; H2O / 24 h / 20 °C 5: 2N aq. KOH, 3percent sodium amalgam / 0.08 h / dark 6: 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