1.1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 2.1: titanium tetrachloride; zinc; 1,1-dibromomethane / tetrahydrofuran; dichloromethane / 5 h / -40 - 20 °C 3.1: K2OsO4*2H2O; methanesulfonamide; potassium carbonate; (DHQ)2PHAL; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 40 h / 0 - 20 °C 4.1: 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 5.1: hydrogenchloride / water / 10 h / Reflux 6.1: potassium tert-butylate / ethylene glycol dimethyl ether / 0.5 h / 20 °C 6.2: 12 h / Reflux 7.1: bis(acetato)bis(triphenylphosphine)palladium(0); potassium acetate / acetonitrile / 12 h / 100 °C / Inert atmosphere View Scheme

1: pyridinium chlorochromate / dichloromethane / 12 h / 20 °C 2: titanium tetrachloride; zinc; 1,1-dibromomethane / tetrahydrofuran; dichloromethane / 5 h / -40 - 20 °C 3: K2OsO4*2H2O; methanesulfonamide; potassium carbonate; (DHQ)2PHAL; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 40 h / 0 - 20 °C 4: 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 5: hydrogenchloride / water / 10 h / Reflux View Scheme