tetrabutyl ammonium fluoride; acetic acid in tetrahydrofuran T=20°C; 336 h;

1.1: (n-Bu)2BOTf; Et3N / CH2Cl2 / 1.33 h / -78 - 0 °C 1.2: CH2Cl2 / 2 h / -78 - 0 °C 1.3: H2O2 / CH2Cl2; aq. phosphate buffer / 20 °C / pH 7.2 2.1: 3.11 g / 2,6-lutidine / CH2Cl2 / 1 h / 20 °C 3.1: 77 percent / NaBH4 / tetrahydrofuran; H2O / 16 h / 25 °C 4.1: 81 percent / pyridine / CH2Cl2 / 1 h / 20 °C 5.1: 44 percent / (Me3Si)3SiH; AIBN / benzene / 4 h / Heating 6.1: 90 percent / AcOH; (n-Bu)4NF / tetrahydrofuran / 336 h / 20 °C View Scheme

1: 81 percent / pyridine / CH2Cl2 / 1 h / 20 °C 2: 44 percent / (Me3Si)3SiH; AIBN / benzene / 4 h / Heating 3: 90 percent / AcOH; (n-Bu)4NF / tetrahydrofuran / 336 h / 20 °C View Scheme

1: 77 percent / NaBH4 / tetrahydrofuran; H2O / 16 h / 25 °C 2: 81 percent / pyridine / CH2Cl2 / 1 h / 20 °C 3: 44 percent / (Me3Si)3SiH; AIBN / benzene / 4 h / Heating 4: 90 percent / AcOH; (n-Bu)4NF / tetrahydrofuran / 336 h / 20 °C View Scheme

1: 44 percent / (Me3Si)3SiH; AIBN / benzene / 4 h / Heating 2: 90 percent / AcOH; (n-Bu)4NF / tetrahydrofuran / 336 h / 20 °C View Scheme

1: potassium carbonate / acetone / 4 h / |Reflux; |Inert atmosphere 2: zinc; ammonium chloride; (R)-TRIP-BINOL / toluene; di-isopropyl ether / 16 h / 4 °C / |Inert atmosphere 3: [RhCl(η2:η2-cycloocta-1,5-diene)]2; triethylamine / 1,4-dioxane; water / 2 h / 90 °C / |Inert atmosphere 4: palladium on activated carbon; hydrogen / ethyl acetate / 16 h / 760.05 Torr / |Inert atmosphere View Scheme

1: zinc; ammonium chloride; (R)-TRIP-BINOL / toluene; di-isopropyl ether / 16 h / 4 °C / |Inert atmosphere 2: [RhCl(η2:η2-cycloocta-1,5-diene)]2; triethylamine / 1,4-dioxane; water / 2 h / 90 °C / |Inert atmosphere 3: palladium on activated carbon; hydrogen / ethyl acetate / 16 h / 760.05 Torr / |Inert atmosphere View Scheme

perchloric acid; hydrogen; palladium on activated charcoal in ethanol P=3040 Torr; 48 h;

Hydrogenation;