1: 1.) Mg, HgCl2 / 1.) THF, 3 h, 0 deg C; 2.) -78 deg C to 0 deg C 2: 81 percent / SOCl2 / diethyl ether / 5 h / Heating 3: 83 percent / NaN3 / dimethylformamide / 3 h / 50 °C 4: 79 percent / H2S / H2O; pyridine / 72 h / Ambient temperature 5: Na/NH3 / tetrahydrofuran / 1 h View Scheme

1: 91 percent / CeCl3 * 7 H2O, sodium borohydride / methanol / 5 h / -75 °C 2: 84 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 48 h / Ambient temperature 3: 81 percent / hydrogen / 10percent Pd-C / methanol; ethyl acetate / Ambient temperature View Scheme

1: 91 percent / CeCl3 * 7 H2O, sodium borohydride / methanol / 5 h / -75 °C 2: 84 percent / m-chloroperoxybenzoic acid / CH2Cl2 / 48 h / Ambient temperature 3: 81 percent / hydrogen / 10percent Pd-C / methanol; ethyl acetate / Ambient temperature View Scheme

sodium hydride; diethyl malonate in tetrahydrofuran T=0 - 20°C;