1: 80 percent / Mo(CO)6, trimethylamine N-oxide, Et3N / diethyl ether / 20 °C 2: 94 percent / I2 / CH2Cl2 / 2 h / -30 °C 3: NaOMe / methanol / 18 h / 20 °C View Scheme

1: 80 percent / Mo(CO)6, trimethylamine N-oxide, Et3N / diethyl ether / 20 °C 2: OsO4, N-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 4 h / 20 °C 3: Et3N / CH2Cl2 / 22 h / 20 °C 4: 65 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 3 h / Heating 5: 42 percent / NaOMe / methanol / 20 h / 20 °C View Scheme

1: 80 percent / Mo(CO)6, trimethylamine N-oxide, Et3N / diethyl ether / 20 °C 2: OsO4, N-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 4 h / 20 °C 3: Et3N / CH2Cl2 / 22 h / 20 °C 4: 65 percent / trimethylsilyl triflate / 1,2-dichloro-ethane / 3 h / Heating 5: 16 percent / NaOMe / methanol / 20 h / 20 °C View Scheme