1: NaBH4 / ethanol / 5 h / 20 °C 2: 77 percent / DMAP / CH2Cl2 / 2 h / 20 °C 3: 83 percent / Bu3SnH; 1,1'-azobis(cyclohexanecarbonitrile) / toluene / 2 h / Heating 4: NaOMe / methanol / 24 h / 100 °C 5: 8 mg / PTSA / dioxane; H2O / 24 h / 120 °C View Scheme

1: 83 percent / Bu3SnH; 1,1'-azobis(cyclohexanecarbonitrile) / toluene / 2 h / Heating 2: NaOMe / methanol / 24 h / 100 °C 3: 8 mg / PTSA / dioxane; H2O / 24 h / 120 °C View Scheme

1: 79 percent / PTSA*H2O / CHCl3 / 6 h / Ambient temperature 2: CuI / tetrahydrofuran / -78 °C 3: Et3N / tetrahydrofuran / -78 - 20 °C 4: 3.54 g / NaI, m-CPBA / tetrahydrofuran / 0.33 h / Ambient temperature 5: Bu3SnH, AIBN / benzene / 1 h / Heating 6: 84 percent / TFA / benzene / 0.33 h 7: BF3*Et2O / CH2Cl2 / 3.5 h 8: 57 mg / DBU / CH2Cl2 / 1 h / Ambient temperature 9: 1.) BH3*Me2S, 2.) H2O2, NaOH / 1.) THF, rt, 4.5 h, 2.) THF, H2O, rt, 12 h 10: CH2Cl2; triethylamine / 1.5 h / Ambient temperature 11: 80 percent / NaN3, 18-crown-6 / dimethylformamide / 1.5 h / 100 °C 12: 94 percent / CrO3, H2SO4 / H2O; acetone / 1.5 h / Ambient temperature 13: 1.) PPh3, 2.) NaBH3CN / 1.) THF, rt, 12 h, 2.) MeOH, AcOH, 12 h 14: 42 percent / H2O; formic acid / 12 h / 120 °C View Scheme

1: 60 percent / MCPBA 2: 77 percent / toluene / 70 °C 3: NaBH4 4: DMAP 5: 83 percent / Bu3SnH, VAZO / toluene 6: NaOMe / methanol / 24 h / 100 °C 7: p-toluenesulfonic acid / dioxane; H2O View Scheme

1: BF3*Et2O / CH2Cl2 / 3.5 h 2: 57 mg / DBU / CH2Cl2 / 1 h / Ambient temperature 3: 1.) BH3*Me2S, 2.) H2O2, NaOH / 1.) THF, rt, 4.5 h, 2.) THF, H2O, rt, 12 h 4: CH2Cl2; triethylamine / 1.5 h / Ambient temperature 5: 80 percent / NaN3, 18-crown-6 / dimethylformamide / 1.5 h / 100 °C 6: 94 percent / CrO3, H2SO4 / H2O; acetone / 1.5 h / Ambient temperature 7: 1.) PPh3, 2.) NaBH3CN / 1.) THF, rt, 12 h, 2.) MeOH, AcOH, 12 h 8: 42 percent / H2O; formic acid / 12 h / 120 °C View Scheme

1: CH2Cl2; triethylamine / 1.5 h / Ambient temperature 2: 80 percent / NaN3, 18-crown-6 / dimethylformamide / 1.5 h / 100 °C 3: 94 percent / CrO3, H2SO4 / H2O; acetone / 1.5 h / Ambient temperature 4: 1.) PPh3, 2.) NaBH3CN / 1.) THF, rt, 12 h, 2.) MeOH, AcOH, 12 h 5: 42 percent / H2O; formic acid / 12 h / 120 °C View Scheme

1: 1.) BH3*Me2S, 2.) H2O2, NaOH / 1.) THF, rt, 4.5 h, 2.) THF, H2O, rt, 12 h 2: CH2Cl2; triethylamine / 1.5 h / Ambient temperature 3: 80 percent / NaN3, 18-crown-6 / dimethylformamide / 1.5 h / 100 °C 4: 94 percent / CrO3, H2SO4 / H2O; acetone / 1.5 h / Ambient temperature 5: 1.) PPh3, 2.) NaBH3CN / 1.) THF, rt, 12 h, 2.) MeOH, AcOH, 12 h 6: 42 percent / H2O; formic acid / 12 h / 120 °C View Scheme

1: Bu3SnH, AIBN / benzene / 1 h / Heating 2: 84 percent / TFA / benzene / 0.33 h 3: BF3*Et2O / CH2Cl2 / 3.5 h 4: 57 mg / DBU / CH2Cl2 / 1 h / Ambient temperature 5: 1.) BH3*Me2S, 2.) H2O2, NaOH / 1.) THF, rt, 4.5 h, 2.) THF, H2O, rt, 12 h 6: CH2Cl2; triethylamine / 1.5 h / Ambient temperature 7: 80 percent / NaN3, 18-crown-6 / dimethylformamide / 1.5 h / 100 °C 8: 94 percent / CrO3, H2SO4 / H2O; acetone / 1.5 h / Ambient temperature 9: 1.) PPh3, 2.) NaBH3CN / 1.) THF, rt, 12 h, 2.) MeOH, AcOH, 12 h 10: 42 percent / H2O; formic acid / 12 h / 120 °C View Scheme

1: 94 percent / CrO3, H2SO4 / H2O; acetone / 1.5 h / Ambient temperature 2: 1.) PPh3, 2.) NaBH3CN / 1.) THF, rt, 12 h, 2.) MeOH, AcOH, 12 h 3: 42 percent / H2O; formic acid / 12 h / 120 °C View Scheme

1: 3.54 g / NaI, m-CPBA / tetrahydrofuran / 0.33 h / Ambient temperature 2: Bu3SnH, AIBN / benzene / 1 h / Heating 3: 84 percent / TFA / benzene / 0.33 h 4: BF3*Et2O / CH2Cl2 / 3.5 h 5: 57 mg / DBU / CH2Cl2 / 1 h / Ambient temperature 6: 1.) BH3*Me2S, 2.) H2O2, NaOH / 1.) THF, rt, 4.5 h, 2.) THF, H2O, rt, 12 h 7: CH2Cl2; triethylamine / 1.5 h / Ambient temperature 8: 80 percent / NaN3, 18-crown-6 / dimethylformamide / 1.5 h / 100 °C 9: 94 percent / CrO3, H2SO4 / H2O; acetone / 1.5 h / Ambient temperature 10: 1.) PPh3, 2.) NaBH3CN / 1.) THF, rt, 12 h, 2.) MeOH, AcOH, 12 h 11: 42 percent / H2O; formic acid / 12 h / 120 °C View Scheme