1.1: hydrogenchloride; water / methanol / 4 h / 20 °C 2.1: sodium periodate / ethanol; water; methanol / 3 h / 20 °C 3.1: copper(II) bis(trifluoromethanesulfonate); borane-THF / 2 h / 20 °C / |Inert atmosphere 4.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 20 °C / |Inert atmosphere 5.1: pyridine / dichloromethane / 1 h / -15 °C / |Inert atmosphere 6.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C 7.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 7.2: 4 h / 20 °C 8.1: pyridine / 2 h / 0 - 20 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / |Inert atmosphere 10.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -78 °C / |Inert atmosphere 10.2: 0.75 h / -78 - 20 °C / |Inert atmosphere 11.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / |Inert atmosphere 11.2: 2 h / 0 °C / |Inert atmosphere 12.1: 10 Pd/C; hydrogen / ethanol / 96 h / 20 °C 13.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 14.1: triethylamine / dichloromethane / 0.75 h / 0 °C 15.1: sodium azide / ethanol; water / 8 h / |Reflux View Scheme

1.1: sodium periodate / ethanol; water; methanol / 3 h / 20 °C 2.1: copper(II) bis(trifluoromethanesulfonate); borane-THF / 2 h / 20 °C / |Inert atmosphere 3.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 20 °C / |Inert atmosphere 4.1: pyridine / dichloromethane / 1 h / -15 °C / |Inert atmosphere 5.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C 6.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 6.2: 4 h / 20 °C 7.1: pyridine / 2 h / 0 - 20 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / |Inert atmosphere 9.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -78 °C / |Inert atmosphere 9.2: 0.75 h / -78 - 20 °C / |Inert atmosphere 10.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / |Inert atmosphere 10.2: 2 h / 0 °C / |Inert atmosphere 11.1: 10 Pd/C; hydrogen / ethanol / 96 h / 20 °C 12.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 13.1: triethylamine / dichloromethane / 0.75 h / 0 °C 14.1: sodium azide / ethanol; water / 8 h / |Reflux View Scheme

1: pyridine / oct-1-ene; ethyl acetate / 6 h / 25 °C 2: Grubb's 2nd generation catalyst / dichloromethane / 14 h / Reflux 3: sodium azide; ammonium chloride / ethanol; water; N,N-dimethyl-formamide / 10 h / 0 - 25 °C 4: triphenylphosphine / toluene / 3 h / Reflux 5: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.75 h / 0 - 25 °C 6: boron trifluoride diethyl etherate / 0.5 h / -10 °C 7: hydrogenchloride / ethanol; water / 12 h / 25 °C 8: triethylamine / dichloromethane / 1 h / 0 °C 9: sodium azide / N,N-dimethyl-formamide / 3 h / 80 °C View Scheme

1: Grubb's 2nd generation catalyst / dichloromethane / 14 h / Reflux 2: sodium azide; ammonium chloride / ethanol; water; N,N-dimethyl-formamide / 10 h / 0 - 25 °C 3: triphenylphosphine / toluene / 3 h / Reflux 4: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.75 h / 0 - 25 °C 5: boron trifluoride diethyl etherate / 0.5 h / -10 °C 6: hydrogenchloride / ethanol; water / 12 h / 25 °C 7: triethylamine / dichloromethane / 1 h / 0 °C 8: sodium azide / N,N-dimethyl-formamide / 3 h / 80 °C View Scheme

1: sodium azide; ammonium chloride / ethanol; water; N,N-dimethyl-formamide / 10 h / 0 - 25 °C 2: triphenylphosphine / toluene / 3 h / Reflux 3: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.75 h / 0 - 25 °C 4: boron trifluoride diethyl etherate / 0.5 h / -10 °C 5: hydrogenchloride / ethanol; water / 12 h / 25 °C 6: triethylamine / dichloromethane / 1 h / 0 °C 7: sodium azide / N,N-dimethyl-formamide / 3 h / 80 °C View Scheme

1: triphenylphosphine / toluene / 3 h / Reflux 2: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0.75 h / 0 - 25 °C 3: boron trifluoride diethyl etherate / 0.5 h / -10 °C 4: hydrogenchloride / ethanol; water / 12 h / 25 °C 5: triethylamine / dichloromethane / 1 h / 0 °C 6: sodium azide / N,N-dimethyl-formamide / 3 h / 80 °C View Scheme

1: boron trifluoride diethyl etherate / 0.5 h / -10 °C 2: hydrogenchloride / ethanol; water / 12 h / 25 °C 3: triethylamine / dichloromethane / 1 h / 0 °C 4: sodium azide / N,N-dimethyl-formamide / 3 h / 80 °C View Scheme

1.1: copper(II) bis(trifluoromethanesulfonate); borane-THF / 0.17 h / 20 °C / |Inert atmosphere 2.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 20 °C / |Inert atmosphere 3.1: pyridine / dichloromethane / 1 h / -15 °C / |Inert atmosphere 4.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C 5.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 5.2: 4 h / 20 °C 6.1: pyridine / 2 h / 0 - 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / |Inert atmosphere 8.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -78 °C / |Inert atmosphere 8.2: 0.75 h / -78 - 20 °C / |Inert atmosphere 9.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / |Inert atmosphere 9.2: 2 h / 0 °C / |Inert atmosphere 10.1: 10 Pd/C; hydrogen / ethanol / 96 h / 20 °C 11.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 12.1: triethylamine / dichloromethane / 0.75 h / 0 °C 13.1: sodium azide / ethanol; water / 8 h / |Reflux View Scheme

1.1: copper(II) bis(trifluoromethanesulfonate); borane-THF / 0.17 h / 20 °C / |Inert atmosphere 2.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 20 °C / |Inert atmosphere 3.1: pyridine / dichloromethane / 1 h / -15 °C / |Inert atmosphere 4.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C 5.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 5.2: 4 h / 20 °C 6.1: pyridine / 2 h / 0 - 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / |Inert atmosphere 8.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -78 °C / |Inert atmosphere 8.2: 0.75 h / -78 - 20 °C / |Inert atmosphere 9.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / |Inert atmosphere 9.2: 2 h / 0 °C / |Inert atmosphere 10.1: 10 Pd/C; hydrogen / ethanol / 96 h / 20 °C 11.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 12.1: triethylamine / dichloromethane / 0.75 h / 0 °C 13.1: sodium azide / ethanol; water / 8 h / |Reflux View Scheme

1.1: triethylsilane; titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / |Inert atmosphere 2.1: 1H-imidazole; 4-(N,N-dimethlyamino)pyridine / dichloromethane / 24 h / 20 °C / |Inert atmosphere 3.1: pyridine / dichloromethane / 1 h / -15 °C / |Inert atmosphere 4.1: sodium azide / N,N-dimethyl-formamide / 2 h / 20 °C 5.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 5.2: 4 h / 20 °C 6.1: pyridine / 2 h / 0 - 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / |Inert atmosphere 8.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 1 h / -78 °C / |Inert atmosphere 8.2: 0.75 h / -78 - 20 °C / |Inert atmosphere 9.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 °C / |Inert atmosphere 9.2: 2 h / 0 °C / |Inert atmosphere 10.1: 10 Pd/C; hydrogen / ethanol / 96 h / 20 °C 11.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 12.1: triethylamine / dichloromethane / 0.75 h / 0 °C 13.1: sodium azide / ethanol; water / 8 h / |Reflux View Scheme