1.1: 4-(N,N-dimethlyamino)pyridine / toluene / 12.25 h / 0 - 20 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C 2.2: 14 h / -78 - 20 °C / Inert atmosphere 3.1: BH3*SMe2 / tetrahydrofuran / 7 h / 40 °C / Inert atmosphere 4.1: water; lithium hydroxide hydrate / ethanol / 5 h / 0 - 20 °C View Scheme

1.1: thionyl chloride / methanol / 3.5 h / 0 - 20 °C 2.1: 4-(N,N-dimethlyamino)pyridine / toluene / 12.25 h / 0 - 20 °C 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C 3.2: 14 h / -78 - 20 °C / Inert atmosphere 4.1: BH3*SMe2 / tetrahydrofuran / 7 h / 40 °C / Inert atmosphere 5.1: water; lithium hydroxide hydrate / ethanol / 5 h / 0 - 20 °C View Scheme

1: [bis(acetoxy)iodo]benzene; palladium diacetate; acetic acid / toluene / 24 h / 110 °C / Inert atmosphere 2: hydrogenchloride; water / 1,4-dioxane / 24 h / 20 °C 3: sodium hydrogencarbonate / 1,4-dioxane / 3 h / 20 °C 4: 10 palladium on activated charcoal; hydrogen / ethyl acetate / 14 h / 20 °C / 760.05 Torr 5: lithium hydroxide hydrate / tetrahydrofuran; methanol; water / 14 h / 20 °C View Scheme

1: hydrogenchloride; water / 1,4-dioxane / 24 h / 20 °C 2: sodium hydrogencarbonate / 1,4-dioxane / 3 h / 20 °C 3: 10 palladium on activated charcoal; hydrogen / ethyl acetate / 14 h / 20 °C / 760.05 Torr 4: lithium hydroxide hydrate / tetrahydrofuran; methanol; water / 14 h / 20 °C View Scheme

1: 10 palladium on activated charcoal; hydrogen / ethyl acetate / 14 h / 20 °C / 760.05 Torr 2: lithium hydroxide hydrate / tetrahydrofuran; methanol; water / 14 h / 20 °C View Scheme

1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C 2: [bis(acetoxy)iodo]benzene; palladium diacetate; acetic acid / toluene / 24 h / 110 °C / Inert atmosphere 3: hydrogenchloride; water / 1,4-dioxane / 24 h / 20 °C 4: sodium hydrogencarbonate / 1,4-dioxane / 3 h / 20 °C 5: 10 palladium on activated charcoal; hydrogen / ethyl acetate / 14 h / 20 °C / 760.05 Torr 6: lithium hydroxide hydrate / tetrahydrofuran; methanol; water / 14 h / 20 °C View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.75 h / -78 °C 1.2: 14 h / -78 - 20 °C / Inert atmosphere 2.1: BH3*SMe2 / tetrahydrofuran / 7 h / 40 °C / Inert atmosphere 3.1: water; lithium hydroxide hydrate / ethanol / 5 h / 0 - 20 °C View Scheme

1: BH3*SMe2 / tetrahydrofuran / 7 h / 40 °C / Inert atmosphere 2: water; lithium hydroxide hydrate / ethanol / 5 h / 0 - 20 °C View Scheme

1: triethylamine / dichloromethane / 0 - 20 °C 2: lithium borohydride / tetrahydrofuran / 20 °C View Scheme

Multistep reaction;