1.1: sodium azide / N,N-dimethyl-formamide / 8 h / 80 °C 2.1: palladium(II) oxide hydrate; hydrogen / methanol / 24 h / 25 °C 3.1: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 °C / |Inert atmosphere; |Reflux 4.1: sodium carbonate / dichloromethane; water / 8 h / |Reflux 5.1: dichloromethane; dimethyl sulfoxide / 1 h / -78 °C / |Inert atmosphere 5.2: 0.25 h / 20 °C / |Inert atmosphere 6.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / |Inert atmosphere 6.2: 48 h / 0 °C / |Inert atmosphere 7.1: sulfuric acid / tetrahydrofuran; water / 12 h / |Reflux 8.1: sodium tetrahydroborate / methanol / 1 h / 0 - 25 °C View Scheme

1.1: palladium(II) oxide hydrate; hydrogen / methanol / 24 h / 25 °C 2.1: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 °C / |Inert atmosphere; |Reflux 3.1: sodium carbonate / dichloromethane; water / 8 h / |Reflux 4.1: dichloromethane; dimethyl sulfoxide / 1 h / -78 °C / |Inert atmosphere 4.2: 0.25 h / 20 °C / |Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / |Inert atmosphere 5.2: 48 h / 0 °C / |Inert atmosphere 6.1: sulfuric acid / tetrahydrofuran; water / 12 h / |Reflux 7.1: sodium tetrahydroborate / methanol / 1 h / 0 - 25 °C View Scheme

1.1: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 °C / |Inert atmosphere; |Reflux 2.1: sodium carbonate / dichloromethane; water / 8 h / |Reflux 3.1: dichloromethane; dimethyl sulfoxide / 1 h / -78 °C / |Inert atmosphere 3.2: 0.25 h / 20 °C / |Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / |Inert atmosphere 4.2: 48 h / 0 °C / |Inert atmosphere 5.1: sulfuric acid / tetrahydrofuran; water / 12 h / |Reflux 6.1: sodium tetrahydroborate / methanol / 1 h / 0 - 25 °C View Scheme

1.1: dichloromethane; dimethyl sulfoxide / 1 h / -78 °C / |Inert atmosphere 1.2: 0.25 h / 20 °C / |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / |Inert atmosphere 2.2: 48 h / 0 °C / |Inert atmosphere 3.1: sulfuric acid / tetrahydrofuran; water / 12 h / |Reflux 4.1: sodium tetrahydroborate / methanol / 1 h / 0 - 25 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / |Inert atmosphere 1.2: 48 h / 0 °C / |Inert atmosphere 2.1: sulfuric acid / tetrahydrofuran; water / 12 h / |Reflux 3.1: sodium tetrahydroborate / methanol / 1 h / 0 - 25 °C View Scheme

1.1: triethylamine / dichloromethane / 1 h / 0 °C / |Inert atmosphere 2.1: sodium azide / N,N-dimethyl-formamide / 8 h / 80 °C 3.1: palladium(II) oxide hydrate; hydrogen / methanol / 24 h / 25 °C 4.1: dimethylsulfide borane complex / tetrahydrofuran / 6 h / 0 °C / |Inert atmosphere; |Reflux 5.1: sodium carbonate / dichloromethane; water / 8 h / |Reflux 6.1: dichloromethane; dimethyl sulfoxide / 1 h / -78 °C / |Inert atmosphere 6.2: 0.25 h / 20 °C / |Inert atmosphere 7.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / |Inert atmosphere 7.2: 48 h / 0 °C / |Inert atmosphere 8.1: sulfuric acid / tetrahydrofuran; water / 12 h / |Reflux 9.1: sodium tetrahydroborate / methanol / 1 h / 0 - 25 °C View Scheme

lithium aluminium tetrahydride in tetrahydrofuran Heating;

1.1: DIAD; PPh3 / tetrahydrofuran / -78 °C 2.1: tetrahydrofuran / 2 h 3.1: H2O2; KF; KHCO3 / 60 - 65 °C 4.1: Imidazole 5.1: O3 / propan-1-ol / -70 °C 5.2: Me2S / propan-1-ol 6.1: NaBH4 / propan-1-ol / 0 °C 7.1: I2; Imidazole; PPh3 8.1: dioxane / 2 h / 115 °C 9.1: 76 percent / Bu4NF View Scheme

1.1: H2O2; KF; KHCO3 / 60 - 65 °C 2.1: Imidazole 3.1: O3 / propan-1-ol / -70 °C 3.2: Me2S / propan-1-ol 4.1: NaBH4 / propan-1-ol / 0 °C 5.1: I2; Imidazole; PPh3 6.1: dioxane / 2 h / 115 °C 7.1: 76 percent / Bu4NF View Scheme

1: I2; Imidazole; PPh3 2: dioxane / 2 h / 115 °C 3: 76 percent / Bu4NF View Scheme