1: tetrabutyl ammonium fluoride / 2 h / 0 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 1 h / 25 °C 3: potassium carbonate / methanol / 2 h / 25 °C 4: pyridine; oct-1-ene; hydrogen / ethyl acetate / 6 h / 20 °C 5: Grubb's 2nd generation catalyst / dichloromethane / 14 h / |Reflux 6: ammonium chloride; sodium azide; water / ethanol; N,N-dimethyl-formamide / 10 h / 0 - 25 °C 7: triphenylphosphine / toluene / 3 h / 110 °C 8: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.75 h / 0 - 25 °C 9: boron trifluoride diethyl etherate / 0.5 h / -10 °C 10: hydrogenchloride / ethanol; water / 12 h / 25 °C 11: triethylamine / dichloromethane / 1 h / 0 °C 12: sodium azide / N,N-dimethyl-formamide / 3 h / 80 °C 13: hydrogen / ethanol / 6 h / 20 °C View Scheme

1: tetrabutyl ammonium fluoride / 2 h / 0 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 1 h / 25 °C 3: potassium carbonate / methanol / 2 h / 25 °C 4: pyridine; oct-1-ene; hydrogen / ethyl acetate / 6 h / 20 °C 5: Grubb's 2nd generation catalyst / dichloromethane / 14 h / |Reflux 6: ammonium chloride; sodium azide; water / ethanol; N,N-dimethyl-formamide / 10 h / 0 - 25 °C 7: triphenylphosphine / toluene / 3 h / 110 °C 8: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.75 h / 0 - 25 °C 9: boron trifluoride diethyl etherate / 0.5 h / -10 °C 10: hydrogenchloride / ethanol; water / 12 h / 25 °C 11: triethylamine / dichloromethane / 1 h / 0 °C 12: sodium azide / N,N-dimethyl-formamide / 3 h / 80 °C View Scheme