Dess-Martin periodane in dichloromethane T=20°C;

1: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -70 deg C, 20 min 2: n-BuLi / diethyl ether; tetrahydrofuran; hexane / 1.) -70 deg C, 20 min, 2.) -70 deg C, 2 h; -50 deg C, 30 min 3: KH / tetrahydrofuran / 1.) r.t., 20 min, 2.) r.t., 20 min 4: toluene / 2 h / Heating 5: H2 / PtO2 / ethyl acetate / 1 h / 2068.6 Torr 6: HCl / ethyl acetate / 1 h / 0 °C View Scheme