sodium hydrogencarbonate; Dess-Martin periodane in dichloromethane T=20°C; 3 h; Inert atmosphere;

10 Pd/C; hydrogen in methanol T=20°C; 10 h;

1.1: zinc / tetrahydrofuran / 0.17 - 0.25 h / 20 °C 1.2: 3 h / 0 °C 2.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetonitrile / 5 h / |Reflux 3.1: dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 0 - 20 °C 3.2: 1 h / 0 °C 4.1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C 5.1: acetic acid / methanol / 1 h / 0 - 20 °C 5.2: 3 h / 0 - 20 °C 6.1: 10 Pd/C; hydrogen / methanol / 10 h / 20 °C View Scheme

1.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / acetonitrile / 5 h / |Reflux 2.1: dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 0 - 20 °C 2.2: 1 h / 0 °C 3.1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C 4.1: acetic acid / methanol / 1 h / 0 - 20 °C 4.2: 3 h / 0 - 20 °C 5.1: 10 Pd/C; hydrogen / methanol / 10 h / 20 °C View Scheme

1.1: dimethylsulfide borane complex / tetrahydrofuran / 1.5 h / 0 - 20 °C 1.2: 1 h / 0 °C 2.1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C 3.1: acetic acid / methanol / 1 h / 0 - 20 °C 3.2: 3 h / 0 - 20 °C 4.1: 10 Pd/C; hydrogen / methanol / 10 h / 20 °C View Scheme

1.1: pyridinium chlorochromate / dichloromethane / 2 h / 20 °C 2.1: acetic acid / methanol / 1 h / 0 - 20 °C 2.2: 3 h / 0 - 20 °C 3.1: 10 Pd/C; hydrogen / methanol / 10 h / 20 °C View Scheme

1.1: acetic acid / methanol / 1 h / 0 - 20 °C 1.2: 3 h / 0 - 20 °C 2.1: 10 Pd/C; hydrogen / methanol / 10 h / 20 °C View Scheme