1: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature 2: Ac2O / CH2Cl2 / 3.5 h / Heating 3: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t. 4: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min 5: 86 percent / Ph3C*BF4 / CH2Cl2 / 48 h / Heating View Scheme

Multi-step reaction with 2 steps 1: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature2: Ac2O / CH2Cl2 / 3.5 h / Heating  

With  sodium hydroxide; sodium ruthenate 0.5 h;  Ambient temperature;   

Multi-step reaction with 4 steps 1: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature2: Ac2O / CH2Cl2 / 3.5 h / Heating3: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t.4: 1) Et3N, 2,4,6-trichlorobenzoyl chloride, 2) 4-(dimethylamino)pyridine / 1) THF, r.t., 3.5 h, 2) THF, toluene, reflux, 10 min  

Multi-step reaction with 3 steps 1: 1) BH3*THF, 2) 3 M NaOH, 30percent H2O2 / 1) THF, 0 deg C, 20 h, 2) THF, r.t., 3 h2: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h3: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer  

Multi-step reaction with 4 steps 1: 83 percent / POCl3, pyridine / 17 h / 85 °C2: 1) BH3*THF, 2) 3 M NaOH, 30percent H2O2 / 1) THF, 0 deg C, 20 h, 2) THF, r.t., 3 h3: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -78 deg C, 2 min, 2) CH2Cl2, -78 deg C, 1 h4: 1 M KMnO4 / 2-methyl-propan-2-ol / 0.08 h / pH 7 phosphate buffer  

Multi-step reaction with 3 steps 1: 86 percent / 1 M NaOH, Na2RuO4 / 0.5 h / Ambient temperature2: Ac2O / CH2Cl2 / 3.5 h / Heating3: 1) Bu2SnO / 1) benzene, reflux, 24 h, 2) toluene, a) -40 deg C, 2 h, b) to r.t.