hydrogen; palladium on activated charcoal in ethanol Ambient temperature;

Grubb's 2nd generation catalyst in dichloromethane T=50°C; 12 h;

boron trifluoride diethyl etherate; mercury(II) oxide; trichloroacetic acid in methanol 2 h; Ambient temperature;

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 - 20 °C 2: 2,6-dimethylpyridine / dichloromethane / 4 h / -78 - 0 °C / Inert atmosphere 3: sodium tetrahydroborate; methanol; cerium(III) chloride heptahydrate / acetone / 1.5 h / -20 - 20 °C 4: triethylamine / dichloromethane / 20 °C 5: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 1 h / -30 - 20 °C / Inert atmosphere 6: sodium methylate / methanol / 1.5 h / 20 °C 7: Dess-Martin periodane / dichloromethane / 5 h / 0 - 20 °C View Scheme

1: 2,6-dimethylpyridine / dichloromethane / 4 h / -78 - 0 °C / Inert atmosphere 2: sodium tetrahydroborate; methanol; cerium(III) chloride heptahydrate / acetone / 1.5 h / -20 - 20 °C 3: triethylamine / dichloromethane / 20 °C 4: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 1 h / -30 - 20 °C / Inert atmosphere 5: sodium methylate / methanol / 1.5 h / 20 °C 6: Dess-Martin periodane / dichloromethane / 5 h / 0 - 20 °C View Scheme

1: sodium tetrahydroborate; methanol; cerium(III) chloride heptahydrate / acetone / 1.5 h / -20 - 20 °C 2: triethylamine / dichloromethane / 20 °C 3: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 1 h / -30 - 20 °C / Inert atmosphere 4: sodium methylate / methanol / 1.5 h / 20 °C 5: Dess-Martin periodane / dichloromethane / 5 h / 0 - 20 °C View Scheme