pyridinium chlorochromate in dichloromethane T=20°C; 1 h;

1: With diisobutylaluminium hydride in hexanes; dichloromethane T=-78°C; 0.75 h; 2: With ammonium chloride in hexanes; dichloromethane; water T=-78 - 20°C;

1.1: sodium periodate / RuCl3 monohydrate / dichloromethane; acetonitrile; water / 5 - 20 °C 2.1: diethylamino-sulfur trifluoride / dichloromethane / 24 h / -10 - 20 °C 3.1: sodium hydroxide; water / pentane; methanol / 75 h / 20 - 60 °C 3.2: pH 1 4.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 5.1: lithium aluminium tetrahydride / tetrahydrofuran / -30 - 20 °C / Inert atmosphere 5.2: 0 °C 6.1: pyridinium chlorochromate / dichloromethane / 1 h / 20 °C View Scheme

1.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / -30 - 20 °C / Inert atmosphere 2.2: 0 °C 3.1: pyridinium chlorochromate / dichloromethane / 1 h / 20 °C View Scheme

1.1: sodium hydroxide; water / pentane; methanol / 75 h / 20 - 60 °C 1.2: pH 1 2.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: lithium aluminium tetrahydride / tetrahydrofuran / -30 - 20 °C / Inert atmosphere 3.2: 0 °C 4.1: pyridinium chlorochromate / dichloromethane / 1 h / 20 °C View Scheme

1.1: diethylamino-sulfur trifluoride / dichloromethane / 24 h / -10 - 20 °C 2.1: sodium hydroxide; water / pentane; methanol / 75 h / 20 - 60 °C 2.2: pH 1 3.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / -30 - 20 °C / Inert atmosphere 4.2: 0 °C 5.1: pyridinium chlorochromate / dichloromethane / 1 h / 20 °C View Scheme