1: pyridine / 2 h / Ambient temperature 2: 1.) BF3-THF complex, 2.) 2N NaOH, 30percent H2O2, 3.) pyridinium chloroformate 3: 209 mg / LiBr / dimethylformamide / 1 h / Heating 4: 220 mg / OsO4, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 3 h 5: 70percent AcOH / H2O / 4 h / 65 °C View Scheme

2: BH3, O2 / tetrahydrofuran / 1.) 0 deg C (1.5 h) , 22 deg C (16 h) 3: 1.) LiCO3, 2.) Jones reagent / 1.) dimethylacetamide, 150 deg C, 15 min 4: OsO4, C5H5N / 3 h / 0 °C 5: 74 percent / CF3CO3H / CH2Cl2 / 1 h / 22 °C View Scheme