1.1: 72 percent / SnCl4 / CH2Cl2 / 8 h / 0 - 25 °C 2.1: 92 percent / Raney Ni / methanol / 3 h / Heating 3.1: 92 percent / LiAlH4 / diethyl ether / 12 h / 25 °C 4.1: 84 percent / imidazole; DMAP / CH2Cl2 / 8 h / 25 °C 5.1: 89 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 25 °C 6.1: toluene / 1 h / -78 °C 6.2: NaH / tetrahydrofuran / 1 h / 0 °C 6.3: TBAI / tetrahydrofuran / 12 h / 25 °C 7.1: 93 percent / TBAF / tetrahydrofuran / 12 h / 25 °C 8.1: 93 percent / iPr2NEt / CH2Cl2 / 8 h / 0 - 25 °C 9.1: OsO4; NMO; pyridine / acetone; H2O / 12 h / 25 °C 9.2: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / 25 °C 10.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 10.2: 77 percent / tetrahydrofuran / 2 h / -78 °C 11.1: 98 percent / TBAF / tetrahydrofuran / 0.5 h / 25 °C 12.1: 91 percent / DDQ / CH2Cl2 / 1 h / 25 °C / pH 7.0 13.1: 93 percent / imidazole; DMAP / CH2Cl2 / 8 h / 40 °C 14.1: n-BuLi / hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 0.5 h / -78 °C 14.2: hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 1 h / -78 °C 15.1: Ph2S / sunlight 16.1: 98 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 25 °C 17.1: 89 percent / DDQ / H2O; CH2Cl2 / 0.5 h / 25 °C / pH 7.0 18.1: 94 percent / TEMPO; bis(acetoxy)iodobenzene / CH2Cl2 / 2 h / 25 °C 19.1: BF3*OEt2 / tetrahydrofuran / 1 h / -78 °C 20.1: 86 percent / iPr2NEt / CH2Cl2 / 12 h / 25 °C 21.1: 88 percent / HF*pyridine / tetrahydrofuran / 12 h / 25 °C 22.1: 83 percent / CF3COOH / CH2Cl2 / 3 h / 0 °C 23.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 25 °C 23.2: 59 percent / DMAP / tetrahydrofuran; toluene / 12 h / 25 °C 24.1: hydroquinone; nBu3SnH / Mo(CO)3(tBuNC)3 / tetrahydrofuran / 12 h / 55 °C 24.2: 54 percent / I2 / CH2Cl2 / 25 °C 25.1: 90 percent / CuI / Pd(PPh3)4 / toluene / 8 h / 80 °C 26.1: 69 percent / Me2BBr / CH2Cl2 / 2 h / -78 °C 27.1: 85 percent / TEMPO; TCCA / CH2Cl2 / 1 h / 25 °C 28.1: NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 0.5 h / 25 °C 29.1: NaBH4; CeCl3*7H2O / methanol / 1 h / 0 °C View Scheme

1: 98 percent / SnCl4 / CH2Cl2 / 24 h / Ambient temperature 2: 88 percent / NaOH / dioxane; H2O / 2 h / Ambient temperature 3: 73 percent / diphenylphosphorylazide, Et3N / 18 h / 80 °C 4: 88 percent / Raney-Nickel / methanol / 4 h / Heating 5: NaOH / dioxane; H2O / 1 h / Ambient temperature View Scheme

hydrogenchloride; methanol; ammonium chloride 1.) MeOH, from 55 to 60 deg C, 2.5 h, 2.) 60 deg C, 3 h; Multistep reaction. Yields of byproduct given;