1.1: Mg / tetrahydrofuran; diethyl ether / 1.5 h / Heating 1.2: 82 percent / tetrahydrofuran; diethyl ether / 2 h / 20 °C 2.1: 84 percent / Br2 / dioxane / 168 h / 20 °C View Scheme

1.1: Mg / tetrahydrofuran; diethyl ether / 1.5 h / Heating 1.2: 82 percent / tetrahydrofuran; diethyl ether / 2 h / 20 °C 2.1: 84 percent / Br2 / dioxane / 168 h / 20 °C 3.1: 72 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C 4.1: 87 percent / MnO2 / CH2Cl2 / 12 h / 20 °C View Scheme

1.1: Mg / tetrahydrofuran; diethyl ether / 1.5 h / Heating 1.2: 82 percent / tetrahydrofuran; diethyl ether / 2 h / 20 °C 2.1: 84 percent / Br2 / dioxane / 168 h / 20 °C 3.1: 72 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C 4.1: 87 percent / MnO2 / CH2Cl2 / 12 h / 20 °C 5.1: aq. m-CPBA / CH2Cl2 / 12 h / 20 °C 6.1: 1.68 g / K2CO3 / methanol / 0.25 h / 20 °C View Scheme

(i) Mg, Et2O, (ii) /BRN= 102378/; Multistep reaction;

N-ethyl-N,N-diisopropylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) in toluene T=45°C;

1.1: 79 percent / Li / tetrahydrofuran / 0.75 h 2.1: 89 percent / PCC; silica gel / CH2Cl2 / 2 h 3.1: 80 percent / tetrahydrofuran / 4 h 4.1: 76 percent / PCC; silica gel / CH2Cl2 / 24 h 5.1: 81 percent / NaBH4 / methanol / 0 - 5 °C 6.1: 45 percent / EtCOOH / 48 h / 180 °C 7.1: 94 percent / PhCH=RuCl2(PCy3)2 / CH2Cl2 / 10 h / 20 °C 8.1: 99 percent / H2 / Pd/C / ethanol / 6 h 9.1: LAH / diethyl ether / 1 h / 0 - 5 °C 9.2: PCC; silica gel / CH2Cl2 / 0.5 h 10.1: 66 percent / (Ph3P)3RhCl / benzene / 24 h / 120 °C View Scheme