1: 80 percent / i-Bu2AlH / toluene / 0 - 20 °C 2: 81 percent / BaMnO4 / CH2Cl2 / 20 °C View Scheme

1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran 2: 96 percent / CrO3, 1.5 M H2SO4 / acetone 3: 100 percent / diethyl phosphorocyanidate, TEA / dimethylformamide / 2 h / 0 °C 4: 98 percent / trifluoroacetic acid / CH2Cl2 / 3 h / Ambient temperature 5: 83 percent / N-iodosuccinimide / dimethylformamide / 12 h / 36 °C 6: 92 percent / n-Bu3SnH / benzene / 0.5 h / Heating 7: 100 percent / 6N aq. HCl / 5 h / Heating View Scheme

tetrabutyl ammonium fluoride in tetrahydrofuran

1: 57 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C 2: 98 percent / CrO3; H2SO4 / acetone; H2O / 0.5 h / 20 °C View Scheme

1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran 2: 96 percent / CrO3, 1.5 M H2SO4 / acetone 3: 100 percent / diethyl phosphorocyanidate, TEA / dimethylformamide / 2 h / 0 °C 4: 98 percent / trifluoroacetic acid / CH2Cl2 / 3 h / Ambient temperature 5: 83 percent / N-iodosuccinimide / dimethylformamide / 12 h / 36 °C 6: 92 percent / n-Bu3SnH / benzene / 0.5 h / Heating 7: 100 percent / 6N aq. HCl / 5 h / Heating 8: methanol View Scheme