triethylamine in dichloromethane; ethyl acetate

ruthenium trichloride; sodium periodate; sodium carbonate in tetrachloromethane; water; acetonitrile

1: aq. Na2CO3, NaHCO3 / dioxane / 1.) 0 deg C, overnight, 2.) 25 deg C, 8 h 2: 26 percent / Jones reagent / acetone / 2 h / 0 °C 3: H2 / 5percent Pd/C / methanol / 3 h View Scheme

1: 91 percent / H2 / Pd(OH)2/C / ethyl acetate 2: 82 percent / RuCl3, NaIO4, Na2CO3, / H2O; acetonitrile; CCl4 View Scheme

dipyridinium dichromate in N,N-dimethyl-formamide T=25°C; 6 h;

hydrogen; palladium on activated charcoal in methanol 3 h;

1: TFA / methanol / 2 h / Ambient temperature 2: aq. Na2CO3, NaHCO3 / dioxane / 1.) 0 deg C, overnight, 2.) 25 deg C, 8 h 3: 26 percent / Jones reagent / acetone / 2 h / 0 °C 4: H2 / 5percent Pd/C / methanol / 3 h View Scheme

1: 26 percent / Jones reagent / acetone / 2 h / 0 °C 2: H2 / 5percent Pd/C / methanol / 3 h View Scheme

1: 68 percent / Na2CO3 / methanol 2: 82 percent / RuCl3, NaIO4, Na2CO3, / H2O; acetonitrile; CCl4 View Scheme

1: PyH*OTs / CH2Cl2 / 24 h / 25 °C 2: NaBH4 / methanol / 1 h / 25 °C 3: 97 percent / pyridine 4: 88 percent / dimethylformamide / 1 h / 0 °C 5: 90 percent / mCPBA 6: PyH*OTs / ethanol / 6 h / 60 °C 7: 95 percent / mCPBA / CH2Cl2 / 1 h / 25 °C 8: 96 percent / PyH*OTs / CH2Cl2 / 24 h / 25 °C 9: 1.) n-BuLi / 1.) THF, -78 deg C; 2.) -50 deg C, 2 h 10: PyH*OTs / ethanol / 6 h / 60 °C 11: 6 percent Na-Hg, Na2HPO4 / methanol / 24 h / 25 °C 12: pyridinium dichromate / dimethylformamide / 6 h / 25 °C View Scheme