1: 95 percent / LiAlH4 / diethyl ether / 0 °C 2: 81 percent / CrO3, pyridine / CH2Cl2 / Ambient temperature 3: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C 5: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 6: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 7: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 8: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 9: 64 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 10: 88 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 95 percent / LiAlH4 / diethyl ether / 0 °C 2: 81 percent / CrO3, pyridine / CH2Cl2 / Ambient temperature 3: 80 percent / BF3*OEt2 / CH2Cl2 / 1.5 h / 0 °C 5: 88.5 percent / p-toluenesulfonic acid / CH2Cl2 / Ambient temperature 6: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 7: 94 percent / pyridine / CHCl3 / a) 0 deg C, 6 h, b) r.t., overnight 8: 1) CuCN / 1) ether, -78 to -40 deg C, 2) ether, -78 to -20 deg C, then 2 h 9: 58 percent / MeI, CaCO3 / acetonitrile; H2O / 24 h / 35 °C 10: 90 percent / p-toluenesulfonic acid / ethanol / 2 h / 55 °C View Scheme

1: 80 percent / LDA / tetrahydrofuran / 1.) from 0 deg C to r.t.; 2.) reflux, 30 min 2: 81 percent / TMEDA, NaH / dimethylsulfoxide / 0.75 h 3: catecholborane / tetrahydrofuran / 4.5 h / -23 °C 4: Raney-Ni / ethanol / 0.5 h / Ambient temperature View Scheme

lithium aluminium tetrahydride in diethyl ether T=0°C;