1: 82 percent / toluene / 2 h / UV-irradiation 2: 86 percent / CrO3*2Py / CH2Cl2 / 1 h / 0 - 25 °C 3: 71 percent / acetic acid / 2 h / UV-irradiation 4: 72 percent / HCl; acetic acid / H2O / 0.5 h / 70 °C 5: 92 percent / OsO4; N-methylmorpholine N-oxide; pyridine / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 12 h 6: 92 percent / 1-hydroxy-1,2-benzodioxol-3(1H)-one 1-oxide / dimethylsulfoxide / 1 h / 20 °C 7: 87 percent / potassium hydroxide; air / H2O; tetrahydrofuran / 1 h View Scheme

titanium tetrachloride in dichloromethane Ambient temperature;

2: 75 percent / NaOH / methanol; H2O 3: 90 percent / TiCl4 / CH2Cl2 / Ambient temperature View Scheme

1: 1.) m-CPBA, 2.) sodium methoxide / 1.) CH2Cl2, reflux, 30 min, 2.) methanol, RT, 30 min 2: 1.) TiCl4 / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, RT, 2.5 h 3: 1.) NaH / 1.) DMF, 15 min, 2.) DMF, RT, 3 h View Scheme

1: 1.) TiCl4 / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, RT, 2.5 h 2: 1.) NaH / 1.) DMF, 15 min, 2.) DMF, RT, 3 h View Scheme

sodium hydride 1.) DMF, 15 min, 2.) DMF, RT, 3 h; Yield given. Multistep reaction;