1: 70 percent / n-BuLi / tetrahydrofuran; hexane / 1.) 0 deg C, 20 min, 2.) 0 deg C, 10 min; room temperature, 30 min 2: 1.) n-BuLi, 2.) red HgO, Celite, BF3*Et2O / 1.) THF, hexane, 0 deg C, 30 min; -30 deg C, 1.5 h, 2.) THF, H2O, room temperature, 1 h View Scheme

n-butyllithium; Celite; boron trifluoride diethyl etherate; mercury(II) oxide 1.) THF, hexane, 0 deg C, 30 min; -30 deg C, 1.5 h, 2.) THF, H2O, room temperature, 1 h; Yield given. Multistep reaction;

1: 81 percent / p-TsOH / acetonitrile / 20 °C 2: 87 percent / MCPBA; NaHCO3 / CH2Cl2 / 0 °C 3: 52 percent / Bu3SnH; AIBN; NaHCO3 / benzene / 2 h / 80 °C View Scheme