1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 70 °C / Inert atmosphere 2: acetic acid; zinc / 34 h / 20 °C / Inert atmosphere View Scheme

1: hydrazine hydrate / ethanol / 3 h / 23 °C / Inert atmosphere 2: hydrogenchloride; zinc / ethanol; water / 3 h / 23 °C / Inert atmosphere 3: potassium carbonate / ethanol / 4 h / 23 °C View Scheme

1: pyridine; 4-(N,N-dimethlyamino)pyridine / 1 h / 150 °C / Inert atmosphere; Microwave irradiation 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 3: hydrazine / ethanol / 10 h / 68 °C / Inert atmosphere View Scheme

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 2: hydrazine / ethanol / 10 h / 68 °C / Inert atmosphere View Scheme

1.1: caesium carbonate / 4 h / 0 - 20 °C 2.1: -15 °C 3.1: trifluoroacetic acid / toluene / 4 h / 20 °C 4.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 0.33 h / 20 °C 5.1: trimethylsilylazide / toluene / 0.33 h / 20 °C 6.1: acetic acid / 48 h / 20 °C 7.1: chloro-trimethyl-silane; zinc / ethanol / 70 °C 7.2: 0 °C 8.1: potassium carbonate / 20 °C View Scheme

1: triethylamine / dichloromethane / 2 h / 0 - 20 °C 2: hydrogenchloride; water / ethanol / 1 h / 50 °C View Scheme

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

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

1.1: triethylamine; 4-(N,N-dimethlyamino)pyridine / 1 h / 0 °C 2.1: sodium hydride / dichloromethane; dimethyl sulfoxide; mineral oil / 8 h / 20 °C 3.1: boron trifluoride diethyl etherate / dichloromethane / 0.37 h / -15 °C 4.1: caesium carbonate / dimethyl sulfoxide / 0.25 h / 80 °C 4.2: 0.33 h / 80 °C View Scheme