1: NaBH4 2: 88 percent / i-Pr2NEt, DMAP / CH2Cl2 / Ambient temperature 3: 1.) n-BuLi / 1.) THF, -78 deg C 4: 39 percent / 3N HCl View Scheme

1: 74 percent / NBS, DBP / CCl4 2: 96 percent / butan-2-one / 0.25 h / Heating 3: NaOH / H2O 4: 3N HCl / 21 h / Heating View Scheme

1: 96 percent / butan-2-one / 0.25 h / Heating 2: NaOH / H2O 3: 3N HCl / 21 h / Heating View Scheme

1: NaOH / H2O 2: 3N HCl / 21 h / Heating View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -65 °C / Inert atmosphere 1.2: 3 h / 20 °C / Inert atmosphere 2.1: potassium borohydride; lithium chloride / tetrahydrofuran / 12 h / 35 °C 3.1: 1H-imidazole / dichloromethane / 1 h / 20 °C 4.1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 5.1: titanium tetrachloride; zinc; 1,1-dibromomethane / tetrahydrofuran; dichloromethane / 5 h / -40 - 20 °C 6.1: K2OsO4*2H2O; methanesulfonamide; potassium carbonate; (DHQ)2PHAL; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 40 h / 0 - 20 °C 7.1: sodium chlorite; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / water; acetonitrile / 5 h / 20 °C / pH 6.7 / aq. phosphate buffer 8.1: hydrogenchloride / water / 10 h / Reflux View Scheme

1: titanium tetrachloride; zinc; 1,1-dibromomethane / tetrahydrofuran; dichloromethane / 5 h / -40 - 20 °C 2: K2OsO4*2H2O; methanesulfonamide; potassium carbonate; (DHQ)2PHAL; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 40 h / 0 - 20 °C 3: sodium chlorite; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / water; acetonitrile / 5 h / 20 °C / pH 6.7 / aq. phosphate buffer 4: hydrogenchloride / water / 10 h / Reflux View Scheme

1: K2OsO4*2H2O; methanesulfonamide; potassium carbonate; (DHQ)2PHAL; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 40 h / 0 - 20 °C 2: sodium chlorite; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / water; acetonitrile / 5 h / 20 °C / pH 6.7 / aq. phosphate buffer 3: hydrogenchloride / water / 10 h / Reflux View Scheme

1: sodium chlorite; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / water; acetonitrile / 5 h / 20 °C / pH 6.7 / aq. phosphate buffer 2: hydrogenchloride / water / 10 h / Reflux View Scheme

1: potassium borohydride; lithium chloride / tetrahydrofuran / 12 h / 35 °C 2: 1H-imidazole / dichloromethane / 1 h / 20 °C 3: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 4: titanium tetrachloride; zinc; 1,1-dibromomethane / tetrahydrofuran; dichloromethane / 5 h / -40 - 20 °C 5: K2OsO4*2H2O; methanesulfonamide; potassium carbonate; (DHQ)2PHAL; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 40 h / 0 - 20 °C 6: sodium chlorite; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / water; acetonitrile / 5 h / 20 °C / pH 6.7 / aq. phosphate buffer 7: hydrogenchloride / water / 10 h / Reflux View Scheme

1: 1H-imidazole / dichloromethane / 1 h / 20 °C 2: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 3: titanium tetrachloride; zinc; 1,1-dibromomethane / tetrahydrofuran; dichloromethane / 5 h / -40 - 20 °C 4: K2OsO4*2H2O; methanesulfonamide; potassium carbonate; (DHQ)2PHAL; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 40 h / 0 - 20 °C 5: sodium chlorite; sodium hypochlorite; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical / water; acetonitrile / 5 h / 20 °C / pH 6.7 / aq. phosphate buffer 6: hydrogenchloride / water / 10 h / Reflux View Scheme