1.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / 0 °C 1.2: 72 percent / hexane; tetrahydrofuran / 48 h / 20 °C 2.1: 92 percent / p-TsOH*H2O / methanol / 20 h / 20 °C 3.1: 69 percent / aq. Jones's reagent / acetone / 2 h / 0 °C View Scheme

in dimethyl sulfoxide; pentane 6 h; Ambient temperature;

1.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / 0 °C 1.2: 72 percent / hexane; tetrahydrofuran / 48 h / 20 °C 2.1: 92 percent / p-TsOH*H2O / methanol / 20 h / 20 °C View Scheme

1: 1) BuLi, 2) HMPA / 1) Et2O, -40 to 20 deg C, 30 min, 2) -40 deg C 2: 79 percent / I2 / diethyl ether 3: deprotection 4: aq. KMnO4 / Bu4NBr / benzene 5: diethyl ether 6: 76 percent / BuLi / -80 °C View Scheme

1: 1.) (i-C3H7)2NLi / 1.) THF, n-hexane, room temp., 3 h, 2.) 55 deg C, 12 h 2: 92 percent / Amberlyst H-15 / methanol / 1 h / 45 °C 3: 95 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 4: MnO2 / CH2Cl2 / 6 h / Ambient temperature 5: 1.) Mg/Hg / 1.) Et2O, 30 min, 2.) room temp., 1 h 6: 98 percent / pyridine / 1 h 7: 88 percent / N2H4*H2O, H2O2 / ethanol / 12 h / 50 - 60 °C View Scheme

sodium iodide in acetone

1H-imidazole; iodine; triphenylphosphine in diethyl ether; acetonitrile

Amberlyst H-15; hydrogen cation in dichloromethane 3 h; Ambient temperature;

1: 99 percent / pyridinium-p-toluene sulphonate / CH2Cl2 / 2 h / 20 °C 2: 91 percent / sodium iodide; NaHCO3 / acetone / 3 h / Heating View Scheme

1: 99 percent / pyridinium-p-toluene sulphonate / CH2Cl2 / 2 h / 20 °C 2: 91 percent / sodium iodide; NaHCO3 / acetone / 3 h / Heating View Scheme