1: OsO4; H2O; 4-methylmorpholine N-oxide / tetrahydrofuran / 48 h / 20 °C 2: 7.8 g / NaIO4 / CH2Cl2 / 1 h 3: NaBH4 / tetrahydrofuran; methanol / 0.33 h / 0 °C 4: 1.84 g / pyridine / CH2Cl2 / 12 h / 0 - 20 °C 5: 71 percent / Pd2(dba)3; Cs2CO3; XANTPHOS / dioxane / 46 h / 110 °C View Scheme

1: 86 percent / CH2Cl2 / 5 h / 0 - 20 °C 2: OsO4; H2O; 4-methylmorpholine N-oxide / tetrahydrofuran / 48 h / 20 °C 3: 7.8 g / NaIO4 / CH2Cl2 / 1 h 4: NaBH4 / tetrahydrofuran; methanol / 0.33 h / 0 °C 5: 1.84 g / pyridine / CH2Cl2 / 12 h / 0 - 20 °C 6: 71 percent / Pd2(dba)3; Cs2CO3; XANTPHOS / dioxane / 46 h / 110 °C View Scheme

4 A molecular sieve; toluene-4-sulfonic acid in chloroform 0.583333 h;

sodium hydroxide

1: bromine / tetrachloromethane / 4.5 h / 20 °C / |Inert atmosphere 2: palladium diacetate; triphenylphosphine; N,N,N',N,-tetramethylethylenediamine; sodium tetrahydroborate / tetrahydrofuran / 1.25 h / 20 °C / |Inert atmosphere 3: palladium diacetate; triphenylphosphine; N,N,N',N,-tetramethylethylenediamine; sodium tetrahydroborate / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere View Scheme

bromine in tetrachloromethane T=20°C; 1.5 h;

bromine in tetrachloromethane T=20°C; 4.5 h;