1: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 2: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 3: 88 percent / tetrahydrofuran / Ambient temperature 5: 1.) CuCN 6: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 7: CrO3, H+ 8: aq. HF / acetonitrile View Scheme

1: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 2: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 3: 88 percent / tetrahydrofuran / Ambient temperature View Scheme

1: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 2: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 3: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 4: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 5: CrO3, H+ View Scheme

1: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 2: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 3: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 4: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 5: CrO3, H+ 7: Bu4NF View Scheme