phosphate-buffered silica gel supported KMnO4 in cyclohexane T=20°C;

lithium methylmercaptide in N,N,N',N',N'',N''-hexamethylphosphoric triamide 12 h; Ambient temperature;

1: 60.5 percent / (dimethylamino)pyridine / CH2Cl2 / 19 h / Ambient temperature 2: 78.8 percent / lithium methyl mercaptide / hexamethylphosphoric acid triamide / 12 h / Ambient temperature View Scheme

1: 60.5 percent / (dimethylamino)pyridine / CH2Cl2 / 19 h / Ambient temperature 2: 78.8 percent / lithium methyl mercaptide / hexamethylphosphoric acid triamide / 12 h / Ambient temperature View Scheme

1: 99 percent / dimethylaluminum chloride / CH2Cl2 / 1 h / Ambient temperature 2: 86 percent / imidazole / dimethylformamide / 2 h 3: 1.) ozonized oxygen; 2.) dimethyl sulfide / 1.) -78 deg C, dichloromethane; 2.) room temp., 12 h 4: 67 percent / potassium t-butoxide, water / diethyl ether / 0.5 h View Scheme

1: 86 percent / imidazole / dimethylformamide / 2 h 2: 1.) ozonized oxygen; 2.) dimethyl sulfide / 1.) -78 deg C, dichloromethane; 2.) room temp., 12 h 3: 67 percent / potassium t-butoxide, water / diethyl ether / 0.5 h View Scheme

1: 1.) ozonized oxygen; 2.) dimethyl sulfide / 1.) -78 deg C, dichloromethane; 2.) room temp., 12 h 2: 67 percent / potassium t-butoxide, water / diethyl ether / 0.5 h View Scheme