palladium on activated charcoal; hydrogen in methanol T=20°C; P=760.051 Torr;

1: NaHSO3 2: pyridine 3: 40 percent / Bacillus sp., glucose / H2O / 48 h / 30 °C 4: LiAlH4 / diethyl ether View Scheme

1: osmium(VIII) oxide; sodium periodate; 2,6-dimethylpyridine / 1,4-dioxane; water / 3 h / 20 °C 2: (+)-6,6'-(((1R,2R,4R,5R)-bicyclo[2.2.2]octane-2,5-diylbis(azanediyl))bis(methylene))bis(2,4-di-tert-butylphenol); (CuOTf)2*C6H5CH3 / methanol / 40 °C / |Molecular sieve 3: hydrogen; palladium on activated charcoal / methanol / 20 °C / 760.05 Torr View Scheme

1: potassium carbonate / acetone / 20 °C 2: osmium(VIII) oxide; sodium periodate; 2,6-dimethylpyridine / 1,4-dioxane; water / 3 h / 20 °C 3: (+)-6,6'-(((1R,2R,4R,5R)-bicyclo[2.2.2]octane-2,5-diylbis(azanediyl))bis(methylene))bis(2,4-di-tert-butylphenol); (CuOTf)2*C6H5CH3 / methanol / 40 °C / |Molecular sieve 4: hydrogen; palladium on activated charcoal / methanol / 20 °C / 760.05 Torr View Scheme

lithium aluminium tetrahydride in diethyl ether

1: pyridine 2: 40 percent / Bacillus sp., glucose / H2O / 48 h / 30 °C 3: LiAlH4 / diethyl ether View Scheme

1: 40 percent / Bacillus sp., glucose / H2O / 48 h / 30 °C 2: LiAlH4 / diethyl ether View Scheme