1: 1) PPh3, DEAD 2: 100 percent / HCl, MeOH / 15 h / 25 °C 3: imidazole / dimethylformamide / 22 h / 25 °C 4: 96 percent / OsO4 (2.5percent in t-BuOH), NaIO4 / tetrahydrofuran; H2O / 22 h / 25 °C 5: 96 percent / KMnO4 / tetrahydrofuran; H2O / 5 h / 25 °C 6: 84 percent / dimethylformamide; acetic acid / 0.75 h / 70 °C 7: 83 percent / ammonium cerium(IV) nitrate / acetonitrile; H2O / 0.2 h / -10 °C View Scheme

1: 30 percent / triphenylphosphine, CH3I, diethyl azodicarboxylate / tetrahydrofuran / 16 h / Ambient temperature 2: 80 percent / tributyltin hydride, 2,2'-azobisisobutyronitrile / benzene / 2 h / Heating 3: OsO4, NaIO4 4: KMnO4 5: 82 percent / dimethylformamide; acetic acid / 1 h / 80 °C 6: 85 percent / aq. (NH4)2Ce(NO3)6 / acetonitrile / 0.75 h / -5 °C View Scheme