pyridinium chlorochromate in dichloromethane T=20°C; 18 h;

toluene-4-sulfonic acid in tetrahydrofuran; water T=20°C; 16 h;

1.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C 2.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 2 h / 70 °C 2.2: pH 3 - 4 3.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / -78 - 60 °C 3.2: -78 - 20 °C 4.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 115 °C 5.1: isobutyramide / 20 °C 6.1: tetrabutyl ammonium fluoride / acetonitrile; tetrahydrofuran / 20 °C 7.1: pyridinium chlorochromate / dichloromethane / 18 h / 20 °C View Scheme

1.1: water; lithium hydroxide hydrate / tetrahydrofuran; methanol / 2 h / 70 °C 1.2: pH 3 - 4 2.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / -78 - 60 °C 2.2: -78 - 20 °C 3.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 115 °C 4.1: isobutyramide / 20 °C 5.1: tetrabutyl ammonium fluoride / acetonitrile; tetrahydrofuran / 20 °C 6.1: pyridinium chlorochromate / dichloromethane / 18 h / 20 °C View Scheme

1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / -78 - 60 °C 1.2: -78 - 20 °C 2.1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 115 °C 3.1: isobutyramide / 20 °C 4.1: tetrabutyl ammonium fluoride / acetonitrile; tetrahydrofuran / 20 °C 5.1: pyridinium chlorochromate / dichloromethane / 18 h / 20 °C View Scheme

1: triethylamine; diphenyl phosphoryl azide / toluene / 1 h / 115 °C 2: isobutyramide / 20 °C 3: tetrabutyl ammonium fluoride / acetonitrile; tetrahydrofuran / 20 °C 4: pyridinium chlorochromate / dichloromethane / 18 h / 20 °C View Scheme

1: tetrabutyl ammonium fluoride / acetonitrile; tetrahydrofuran / 20 °C 2: pyridinium chlorochromate / dichloromethane / 18 h / 20 °C View Scheme

hydrogen; acetic acid; platinum(IV) oxide T=20°C; 8 h;