1: 1.) DCC, CuCl / 1.) dioxane, 45-50 deg C, 48 h, 2.) toluene, reflux, 24 h 2: 92 percent / aq. NaOH / tetrahydrofuran / 0.5 h / 25 °C View Scheme

1: sodium carbonate / dichloromethane; water / 8 h / 20 °C 2: hydrogenchloride; acetic acid / water / 0.5 h / Reflux 3: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Reflux 4: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 20 °C 5: sodium dihydrogenphosphate; sodium chlorite; water / methyl-2-butene; tert-butyl alcohol / 1.5 h / 0 - 20 °C View Scheme

1: hydrogenchloride; acetic acid / water / 0.5 h / Reflux 2: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Reflux 3: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 20 °C 4: sodium dihydrogenphosphate; sodium chlorite; water / methyl-2-butene; tert-butyl alcohol / 1.5 h / 0 - 20 °C View Scheme

1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Reflux 2: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 20 °C 3: sodium dihydrogenphosphate; sodium chlorite; water / methyl-2-butene; tert-butyl alcohol / 1.5 h / 0 - 20 °C View Scheme

1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 2 h / 20 °C 2: sodium dihydrogenphosphate; sodium chlorite; water / methyl-2-butene; tert-butyl alcohol / 1.5 h / 0 - 20 °C View Scheme

T=0 - 5°C;

1: HBr, AcOH 3: 1) DAST, 2) RuO4 4: 1) HCl, 2) Ag2O View Scheme

1: 83 percent / p-toluenesulfonic acid / 36 h / Heating 2: 80 percent / pyridine / CHCl3 / 168 h / Ambient temperature 3: 70 percent / dimethylsulfoxide / 3 h / 80 °C 4: 94 percent / HCl / 96 h 5: 100 percent / 4 M NaOH / tetrahydrofuran; H2O / 0.92 h 6: 75 percent / H2 / 10percent Pd/C / methanol / 0.5 h / 2482.3 - 2585.7 Torr View Scheme

palladium 10 on activated carbon; hydrogen in methanol T=20°C; P=760.051 Torr; 4 h;

boron dimethyl-trifluoro sulphide in tetrahydrofuran T=0 - 20°C; 2.5 h;