1: 1.) n-BuLi, (-)-sparteine / 1.) toluene, -78 deg C, 4 h, 2.) toluene, -78 deg C -> room temperature 2: ammonium cerium(IV) nitrate / acetonitrile; H2O / 0.5 h / 0 °C View Scheme

1: 1.) n-BuLi, (-)-sparteine / 1.) toluene, -78 deg C, 4 h, 2.) toluene, -78 deg C -> room temperature 2: ammonium cerium(IV) nitrate / acetonitrile; H2O / 0.5 h / 0 °C 3: NaIO4, RuCl3*H2O / CCl4; acetonitrile; H2O / 48 h / Ambient temperature 4: 1.) thionyl chloride, 2.) di-tert-butyl dicarbonate / 1.) 2 h, 2.) CH2Cl2 View Scheme

1: 1.) n-BuLi, (-)-sparteine / 1.) toluene, -78 deg C, 4 h, 2.) toluene, -78 deg C -> room temperature 2: ammonium cerium(IV) nitrate / acetonitrile; H2O / 0.5 h / 0 °C 3: NaIO4, RuCl3*H2O / CCl4; acetonitrile; H2O / 48 h / Ambient temperature View Scheme