1: sodium periodate; ruthenium(III) chloride*(x)H2O / tetrachloromethane; acetonitrile; water / 1 h / 20 °C 2: sulfuric acid / 1,4-dioxane / 12 h / 0 °C / |Reflux View Scheme

1: sodium periodate; ruthenium(III) chloride*(x)H2O / tetrachloromethane; acetonitrile; water / 1 h / 20 °C 2: sulfuric acid / 1,4-dioxane / 12 h / 0 °C / |Reflux 3: tetrahydrofuran / 2 h / 0 °C View Scheme

1: n-butyllithium; borane-ammonia complex; diisopropylamine / tetrahydrofuran / 2 h / 0 °C 2: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / tetrahydrofuran / 18 h / 20 °C 3: sodium periodate; ruthenium(III) chloride*(x)H2O / tetrachloromethane; acetonitrile; water / 1 h / 20 °C 4: borane-THF / tetrahydrofuran / 3.5 h / 20 °C 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C View Scheme

1: n-butyllithium; borane-ammonia complex; diisopropylamine / tetrahydrofuran / 2 h / 0 °C 2: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / tetrahydrofuran / 18 h / 20 °C 3: sodium periodate; ruthenium(III) chloride*(x)H2O / tetrachloromethane; acetonitrile; water / 1 h / 20 °C 4: borane-THF / tetrahydrofuran / 3.5 h / 20 °C 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C View Scheme