sodium hydroxide in methanol T=4°C; 24 h;

1.1: potassium carbonate / dichloromethane; methanol / 16 h / Reflux 2.1: triethylamine / dichloromethane / 1 h / 20 °C 3.1: oxygen / palladium diacetate / dichloromethane; dimethyl sulfoxide / 35 °C 4.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 1 h / 20 °C 4.2: 2 h / 0 - 8 °C 5.1: pyridine / 4-(N,N-dimethlyamino)pyridine / 2 h / 20 °C 6.1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C 7.1: hydrogen / palladium 10 on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr 8.1: potassium carbonate; methanol / 4 h / 20 °C View Scheme

1.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 1 h / 20 °C 1.2: 2 h / 0 - 8 °C 2.1: pyridine / 4-(N,N-dimethlyamino)pyridine / 2 h / 20 °C 3.1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C 4.1: hydrogen / palladium 10 on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr 5.1: potassium carbonate; methanol / 4 h / 20 °C View Scheme

1.1: triethylamine / dichloromethane / 1 h / 20 °C 2.1: oxygen / palladium diacetate / dichloromethane; dimethyl sulfoxide / 35 °C 3.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 1 h / 20 °C 3.2: 2 h / 0 - 8 °C 4.1: pyridine / 4-(N,N-dimethlyamino)pyridine / 2 h / 20 °C 5.1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C 6.1: hydrogen / palladium 10 on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr 7.1: potassium carbonate; methanol / 4 h / 20 °C View Scheme

1.1: oxygen / palladium diacetate / dichloromethane; dimethyl sulfoxide / 35 °C 2.1: cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 1 h / 20 °C 2.2: 2 h / 0 - 8 °C 3.1: pyridine / 4-(N,N-dimethlyamino)pyridine / 2 h / 20 °C 4.1: trimethylamine-N-oxide / ~5percent w/w OsO4 on PVP / tetrahydrofuran / 50 °C 5.1: hydrogen / palladium 10 on activated carbon / methanol / 24 h / 20 °C / 760.05 Torr 6.1: potassium carbonate; methanol / 4 h / 20 °C View Scheme

1: 46 percent / OsO4 / benzene; pyridine / Ambient temperature 2: 21 mg / 1 N NaOH / methanol / 24 h / 4 °C View Scheme