1: HMPA, Ph3CH, n-BuLi / tetrahydrofuran / 48 h / Heating 2: H2 / Pd/CaCO3/Pb / benzene / 12 h / 760 Torr 3: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 4: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

1: H2 / Pd/CaCO3/Pb / benzene / 12 h / 760 Torr 2: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 3: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

1: HMPA, Ph3CH, n-BuLi / tetrahydrofuran / 48 h / Heating 2: H2 / Pd/CaCO3/Pb / benzene / 12 h / 760 Torr 3: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 4: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

ammonium cerium(IV) nitrate in water; acetonitrile 1.) -7 deg C, 1 h, 2.) room temp., 2 h;

1: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 2: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

1: mCPBA / 2 h / Ambient temperature 2: aq. KOH / ethanol / 2 h / 50 °C 3: 94 percent / NaH / dimethylformamide / 1 h / Ambient temperature 4: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 5: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

1: 94 percent / NaH / dimethylformamide / 1 h / Ambient temperature 2: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 3: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

1: 1.) HMPA, n-BuLi / 1.) THF, hexane, -40 deg C, 30 min, then -40 to -10 deg C, 1 h, -10 deg C, 1h, 2.) THF, hexane, overnight 2: 1.) ammonium cerium(IV) nitrate, 2.) HClO4 / 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h View Scheme

perchloric acid; ammonium cerium(IV) nitrate 1.) CH3CN, H2O, -7 deg C, 1 h, then room temp., 2 h, 2.) CH2Cl2, room temp., 4 h; Yield given. Multistep reaction;