formic acid in water Reflux;

1.1: iodine; magnesium / tetrahydrofuran / 5 h / 80 - 85 °C / Reflux 2.1: tetrahydrofuran / 0.25 h / -5 °C 2.2: 0.5 h / -5 - 20 °C 2.3: pH 2 3.1: isopropyl alcohol / 3 h / 20 - 45 °C 4.1: ammonia / water / pH ~ 9 4.2: 3 h / -5 °C View Scheme

1.1: tetrahydrofuran / 0.25 h / -5 °C 1.2: 0.5 h / -5 - 20 °C 1.3: pH 2 2.1: isopropyl alcohol / 3 h / 20 - 45 °C 3.1: ammonia / water / pH ~ 9 3.2: 3 h / -5 °C View Scheme

1.1: potassium hydroxide / water / 0 - 5 °C 1.2: 4 h / 100 - 110 °C / Reflux 2.1: tetrahydrofuran / 0.25 h / -5 °C 2.2: 0.5 h / -5 - 20 °C 2.3: pH 2 3.1: isopropyl alcohol / 3 h / 20 - 45 °C 4.1: ammonia / water / pH ~ 9 4.2: 3 h / -5 °C View Scheme

1.1: tetrahydrofuran / 0.25 h / -5 °C 1.2: 0.5 h / -5 - 20 °C 1.3: pH 2 2.1: isopropyl alcohol / 3 h / 20 - 45 °C 3.1: ammonia / water / pH ~ 9 3.2: 3 h / -5 °C View Scheme

1.1: toluene-4-sulfonic acid / dichloromethane / 15 h / 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.17 h / -98 °C / Inert atmosphere 2.2: 1.67 h / -98 - 20 °C / Inert atmosphere 3.1: water / tetrahydrofuran / 1 h / 20 °C 4.1: magnesium sulfate / dichloromethane / 15 h / 20 °C / Inert atmosphere 5.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / -78 °C / Inert atmosphere 5.2: -98 - -78 °C / Inert atmosphere 6.1: toluene-4-sulfonic acid / diethyl ether / Inert atmosphere; Reflux 7.1: water; sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 16 h / 20 °C View Scheme

1.1: water; sodium hydroxide / methanol / 4 h 2.1: toluene-4-sulfonic acid / dichloromethane / 15 h / 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran / 0.17 h / -98 °C / Inert atmosphere 3.2: 1.67 h / -98 - 20 °C / Inert atmosphere 4.1: water / tetrahydrofuran / 1 h / 20 °C 5.1: magnesium sulfate / dichloromethane / 15 h / 20 °C / Inert atmosphere 6.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / -78 °C / Inert atmosphere 6.2: -98 - -78 °C / Inert atmosphere 7.1: toluene-4-sulfonic acid / diethyl ether / Inert atmosphere; Reflux 8.1: water; sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 16 h / 20 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran / 0.17 h / -98 °C / Inert atmosphere 1.2: 1.67 h / -98 - 20 °C / Inert atmosphere 2.1: water / tetrahydrofuran / 1 h / 20 °C 3.1: magnesium sulfate / dichloromethane / 15 h / 20 °C / Inert atmosphere 4.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / -78 °C / Inert atmosphere 4.2: -98 - -78 °C / Inert atmosphere 5.1: toluene-4-sulfonic acid / diethyl ether / Inert atmosphere; Reflux 6.1: water; sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 16 h / 20 °C View Scheme

1.1: N,N,N',N,-tetramethylethylenediamine; sec.-butyllithium / diethyl ether / -78 °C / Inert atmosphere 1.2: -98 - -78 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / diethyl ether / Inert atmosphere; Reflux 3.1: water; sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 16 h / 20 °C View Scheme

1: toluene-4-sulfonic acid / diethyl ether / Inert atmosphere; Reflux 2: water; sodium tris(acetoxy)borohydride; acetic acid / dichloromethane / 16 h / 20 °C View Scheme