water; lithium chloride in dimethyl sulfoxide T=90°C; 16 h;

1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tert-butyl alcohol; tetrahydrofuran / 6 h / 25 °C 2: sodium periodate; water / tert-butyl alcohol; tetrahydrofuran / 8 h / 25 °C 3: toluene-4-sulfonic acid / toluene / 25 - 120 °C 4: hydrogen / palladium on carbon / ethanol / 25 °C / Inert atmosphere 5: water; lithium chloride / dimethyl sulfoxide / 16 h / 90 °C View Scheme

1: toluene-4-sulfonic acid / toluene / 25 - 120 °C 2: hydrogen / palladium on carbon / ethanol / 25 °C / Inert atmosphere 3: water; lithium chloride / dimethyl sulfoxide / 16 h / 90 °C View Scheme

1: hydrogen / palladium on carbon / ethanol / 25 °C / Inert atmosphere 2: water; lithium chloride / dimethyl sulfoxide / 16 h / 90 °C View Scheme

1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 16 h / 110 °C / Inert atmosphere 2: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tert-butyl alcohol; tetrahydrofuran / 6 h / 25 °C 3: sodium periodate; water / tert-butyl alcohol; tetrahydrofuran / 8 h / 25 °C 4: toluene-4-sulfonic acid / toluene / 25 - 120 °C 5: hydrogen / palladium on carbon / ethanol / 25 °C / Inert atmosphere 6: water; lithium chloride / dimethyl sulfoxide / 16 h / 90 °C View Scheme