hydrogen; palladium on activated charcoal in ethanol; water P=2068.6 Torr; 24 h;

sodium hydroxide in 1,4-dioxane T=20°C;

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

jones' reagent in acetone T=20°C; 24 h;

1: 74 percent / triphenylphosphine; diethyl azodicarboxylate; diphenyl phosphoryl azide / tetrahydrofuran / 6 h / 20 °C 2: hydrogen / 10 percent Pd/C / ethanol / 24 h / 20 °C / 760 Torr 3: 0.838 g / ethanol / 6 h / 20 °C 4: 50 percent / Jones' reagent / acetone / 24 h / 20 °C View Scheme

1: hydrogen / 10 percent Pd/C / ethanol / 24 h / 20 °C / 760 Torr 2: 0.838 g / ethanol / 6 h / 20 °C 3: 50 percent / Jones' reagent / acetone / 24 h / 20 °C View Scheme

1: 73 percent / H2 / Pd(OH)2 / 8 h / 20 °C 2: RuCl3; aq. NaIO4 / CCl4; acetonitrile / 8 h View Scheme

1: 73 percent / H2 / Pd(OH)2 / 8 h / 20 °C 2: RuCl3; aq. NaIO4 / CCl4; acetonitrile / 8 h View Scheme

1: LiAlH4 / diethyl ether / 0 °C 2: 73 percent / H2 / Pd(OH)2 / 8 h / 20 °C 3: RuCl3; aq. NaIO4 / CCl4; acetonitrile / 8 h View Scheme

1: 90 percent / pyridine 2: dimethylformamide / 1 h / 0 °C 3: 92 percent / NaBH4 / methanol / 1 h / 25 °C 4: 93 percent / mCPBA / CH2Cl2 / 1 h / 25 °C 5: 95 percent / PyH*OTs / CH2Cl2 / 24 h / 25 °C 6: 1.) n-BuLi / 1.) THF, -78 deg C; 2.) -50 deg C, 2 h 7: 93 percent / PyH*OTs / ethanol / 6 h / 60 °C 8: 92 percent / 6percent Na-Hg, Na2HPO4 / methanol / 24 h / 25 °C 9: 78 percent / pyridinium dichromate / dimethylformamide / 6 h / 25 °C View Scheme