1: 60 percent / pyridinium chlorochromate / NaOAc / CH2Cl2 / 2 h / Ambient temperature 2: 1) NaH / 1) THF, below 20 deg C 2a) r.t., 6h 2b) 60 deg C, 3h 3: 60 percent / LiAlH4 / benzene / 1) r.t., 2h 2) 60 deg C, 12h 4: 94 percent / NEt3 / CH2Cl2 / 0.5 h / 0 °C 5: 40 percent / CuI / diethyl ether / 1) 0 deg C, 4 h 2) r.t. 6: 95 percent / conc.HCl / methanol / 4 h View Scheme

1: 95 percent / Bu3P, CCl4 2: 1.) Mg / 1.) THF, reflux, 5 h, 2.) r.t., 3.5 h 3: 1.) Mg / 2.) Li2CuCl4 / 1.) Et2O, reflux, 2 h, 2.) THF, 0 deg C, 3 h 4: 94 percent / PPh3, Br2 / CH2Cl2 / 36 h / Ambient temperature View Scheme