1: 95 percent / mCPBA / CH2Cl2 / 1 h / 25 °C 2: 96 percent / PyH*OTs / CH2Cl2 / 24 h / 25 °C 3: 1.) n-BuLi / 1.) THF, -78 deg C; 2.) -50 deg C, 2 h 4: PyH*OTs / ethanol / 6 h / 60 °C 5: 6 percent Na-Hg, Na2HPO4 / methanol / 24 h / 25 °C 6: pyridinium dichromate / dimethylformamide / 6 h / 25 °C View Scheme

1: 1.) n-BuLi / 1.) THF, -78 deg C; 2.) -50 deg C, 2 h 2: PyH*OTs / ethanol / 6 h / 60 °C 3: 6 percent Na-Hg, Na2HPO4 / methanol / 24 h / 25 °C 4: pyridinium dichromate / dimethylformamide / 6 h / 25 °C View Scheme

1: 97 percent / pyridine 2: 88 percent / dimethylformamide / 1 h / 0 °C 3: 90 percent / mCPBA 4: PyH*OTs / ethanol / 6 h / 60 °C 5: 95 percent / mCPBA / CH2Cl2 / 1 h / 25 °C 6: 96 percent / PyH*OTs / CH2Cl2 / 24 h / 25 °C 7: 1.) n-BuLi / 1.) THF, -78 deg C; 2.) -50 deg C, 2 h 8: PyH*OTs / ethanol / 6 h / 60 °C 9: 6 percent Na-Hg, Na2HPO4 / methanol / 24 h / 25 °C 10: pyridinium dichromate / dimethylformamide / 6 h / 25 °C View Scheme

1: NaBH4 / methanol / 1 h / 25 °C 2: 97 percent / pyridine 3: 88 percent / dimethylformamide / 1 h / 0 °C 4: 90 percent / mCPBA 5: PyH*OTs / ethanol / 6 h / 60 °C 6: 95 percent / mCPBA / CH2Cl2 / 1 h / 25 °C 7: 96 percent / PyH*OTs / CH2Cl2 / 24 h / 25 °C 8: 1.) n-BuLi / 1.) THF, -78 deg C; 2.) -50 deg C, 2 h 9: PyH*OTs / ethanol / 6 h / 60 °C 10: 6 percent Na-Hg, Na2HPO4 / methanol / 24 h / 25 °C 11: pyridinium dichromate / dimethylformamide / 6 h / 25 °C View Scheme

1: 90 percent / mCPBA 2: PyH*OTs / ethanol / 6 h / 60 °C 3: 95 percent / mCPBA / CH2Cl2 / 1 h / 25 °C 4: 96 percent / PyH*OTs / CH2Cl2 / 24 h / 25 °C 5: 1.) n-BuLi / 1.) THF, -78 deg C; 2.) -50 deg C, 2 h 6: PyH*OTs / ethanol / 6 h / 60 °C 7: 6 percent Na-Hg, Na2HPO4 / methanol / 24 h / 25 °C 8: pyridinium dichromate / dimethylformamide / 6 h / 25 °C View Scheme

1: 88 percent / dimethylformamide / 1 h / 0 °C 2: 90 percent / mCPBA 3: PyH*OTs / ethanol / 6 h / 60 °C 4: 95 percent / mCPBA / CH2Cl2 / 1 h / 25 °C 5: 96 percent / PyH*OTs / CH2Cl2 / 24 h / 25 °C 6: 1.) n-BuLi / 1.) THF, -78 deg C; 2.) -50 deg C, 2 h 7: PyH*OTs / ethanol / 6 h / 60 °C 8: 6 percent Na-Hg, Na2HPO4 / methanol / 24 h / 25 °C 9: pyridinium dichromate / dimethylformamide / 6 h / 25 °C View Scheme

1: 96 percent / PyH*OTs / CH2Cl2 / 24 h / 25 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C; 2.) -50 deg C, 2 h 3: PyH*OTs / ethanol / 6 h / 60 °C 4: 6 percent Na-Hg, Na2HPO4 / methanol / 24 h / 25 °C 5: pyridinium dichromate / dimethylformamide / 6 h / 25 °C View Scheme

1: 6 percent Na-Hg, Na2HPO4 / methanol / 24 h / 25 °C 2: pyridinium dichromate / dimethylformamide / 6 h / 25 °C View Scheme

1: PyH*OTs / ethanol / 6 h / 60 °C 2: 6 percent Na-Hg, Na2HPO4 / methanol / 24 h / 25 °C 3: pyridinium dichromate / dimethylformamide / 6 h / 25 °C View Scheme

ruthenium trichloride; sodium periodate; hydrogen; sodium carbonate; palladium dihydroxide 1.) CH3COOEt; 2.) CH3CN, CCl4, H2O; Yield given. Multistep reaction;