1.1: NaH / tetrahydrofuran / 1.5 h / 0 °C 1.2: tetrabutylammonium iodide / tetrahydrofuran / 4 h / 20 °C 2.1: p-TsOH / methanol / 3 h / 20 °C 3.1: IBX / tetrahydrofuran; dimethylsulfoxide / 4 h / 20 °C 4.1: NaH / tetrahydrofuran / 0.17 h / 0 °C 4.2: 2.86 g / tetrahydrofuran / 0.5 h / Heating 5.1: DIBAL-H / tetrahydrofuran / 5 h / 20 °C 6.1: PdCl2(MeCN)2 / tetrahydrofuran / 3 h / 20 °C 7.1: O3 / CH2Cl2; methanol / -78 °C 7.2: NaBH4 / CH2Cl2; methanol / -78 - 20 °C 8.1: aq. HCl / methanol / 5 h / 70 °C 9.1: H2 / Pd/C / acetic acid / 48 h / 20 °C View Scheme

1.1: 99 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 °C 2.1: 89 percent / imidazole / dimethylformamide / 3 h / 20 °C 3.1: AD-mix-β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 20 h / 0 °C 4.1: NaH / tetrahydrofuran / 1.5 h / 0 °C 4.2: tetrabutylammonium iodide / tetrahydrofuran / 4 h / 20 °C 5.1: p-TsOH / methanol / 3 h / 20 °C 6.1: IBX / tetrahydrofuran; dimethylsulfoxide / 4 h / 20 °C 7.1: NaH / tetrahydrofuran / 0.17 h / 0 °C 7.2: 2.86 g / tetrahydrofuran / 0.5 h / Heating 8.1: DIBAL-H / tetrahydrofuran / 5 h / 20 °C 9.1: PdCl2(MeCN)2 / tetrahydrofuran / 3 h / 20 °C 10.1: O3 / CH2Cl2; methanol / -78 °C 10.2: NaBH4 / CH2Cl2; methanol / -78 - 20 °C 11.1: aq. HCl / methanol / 5 h / 70 °C 12.1: H2 / Pd/C / acetic acid / 48 h / 20 °C View Scheme

1.1: 78 percent / Super-Hydride / tetrahydrofuran / 3 h / 0 °C 2.1: HCl / methanol; H2O / 2 h / 60 °C 2.2: 83 percent / DOWEX-50wX8 View Scheme

1.1: 82 percent / m-CPBA; NaH2PO4 / CH2Cl2 / 20 °C 2.1: 78 percent / imidazole; 4-(dimethylamino)pyridine / CH2Cl2 / 20 °C 3.1: KOH / dioxane 3.2: 17 percent / HCl / methanol / 1 h / 60 °C View Scheme

1.1: 78 percent / imidazole; 4-(dimethylamino)pyridine / CH2Cl2 / 20 °C 2.1: KOH / dioxane 2.2: 17 percent / HCl / methanol / 1 h / 60 °C View Scheme

hydrogenchloride T=100°C; 2 h;

1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 0.13 h / -78 °C / Inert atmosphere 1.3: -78 - 30 °C / Inert atmosphere 2.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C 3.1: potassium carbonate / methanol / 1 h / 30 °C / Inert atmosphere 3.2: Inert atmosphere 3.3: Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 1 h / 30 °C / Inert atmosphere 4.2: Inert atmosphere 5.1: lithium aluminium tetrahydride / diethyl ether / 0 °C / Reflux; Inert atmosphere 5.2: 15 h / 60 °C / Inert atmosphere View Scheme

1.1: potassium carbonate / methanol / 1 h / 30 °C / Inert atmosphere 1.2: Inert atmosphere 1.3: Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 1 h / 30 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: lithium aluminium tetrahydride / diethyl ether / 0 °C / Reflux; Inert atmosphere 3.2: 15 h / 60 °C / Inert atmosphere View Scheme

1.1: palladium 10 on activated carbon; hydrogen / ethyl acetate / 24 h / 20 °C 2.1: potassium carbonate / methanol / 1 h / 30 °C / Inert atmosphere 2.2: Inert atmosphere 2.3: Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 1 h / 30 °C / Inert atmosphere 3.2: Inert atmosphere 4.1: lithium aluminium tetrahydride / diethyl ether / 0 °C / Reflux; Inert atmosphere 4.2: 15 h / 60 °C / Inert atmosphere View Scheme

1.1: trifluoroacetic acid / dichloromethane / 1 h / 30 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: lithium aluminium tetrahydride / diethyl ether / 0 °C / Reflux; Inert atmosphere 2.2: 15 h / 60 °C / Inert atmosphere View Scheme