trichlorophosphate in N,N-dimethyl-formamide T=20°C; 3.5 h;

trichlorophosphate 1) 15 min., 0 deg C, 2) 2.5 h, room temp.;

silver nitrate in water; acetone T=40°C; 24 h;

trichloroacetic acid in acetone T=40°C; 1 h;

1: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) reflux 2: 99 percent / diethyl ether / Ambient temperature 3: 88 percent / Et3N, TMSOTf / CH2Cl2 / 16 h / Heating 4: 97 percent / Dess-Martin periodinane reagent / CH2Cl2 / Ambient temperature 5: 91 percent / AgNO3, CaCO3 / acetone; H2O / Ambient temperature 6: 90 percent / DIBAH / diethyl ether / 0 °C 7: 41 percent / AgNO3 / acetone; H2O / 24 h / 40 °C View Scheme

1: 99 percent / diethyl ether / Ambient temperature 2: 88 percent / Et3N, TMSOTf / CH2Cl2 / 16 h / Heating 3: 97 percent / Dess-Martin periodinane reagent / CH2Cl2 / Ambient temperature 4: 91 percent / AgNO3, CaCO3 / acetone; H2O / Ambient temperature 5: 90 percent / DIBAH / diethyl ether / 0 °C 6: 41 percent / AgNO3 / acetone; H2O / 24 h / 40 °C View Scheme

1: 90 percent / DIBAH / diethyl ether / 0 °C 2: 41 percent / AgNO3 / acetone; H2O / 24 h / 40 °C View Scheme

1: 97 percent / Dess-Martin periodinane reagent / CH2Cl2 / Ambient temperature 2: 91 percent / AgNO3, CaCO3 / acetone; H2O / Ambient temperature 3: 90 percent / DIBAH / diethyl ether / 0 °C 4: 41 percent / AgNO3 / acetone; H2O / 24 h / 40 °C View Scheme

1: 91 percent / AgNO3, CaCO3 / acetone; H2O / Ambient temperature 2: 90 percent / DIBAH / diethyl ether / 0 °C 3: 41 percent / AgNO3 / acetone; H2O / 24 h / 40 °C View Scheme

1: 88 percent / Et3N, TMSOTf / CH2Cl2 / 16 h / Heating 2: 97 percent / Dess-Martin periodinane reagent / CH2Cl2 / Ambient temperature 3: 91 percent / AgNO3, CaCO3 / acetone; H2O / Ambient temperature 4: 90 percent / DIBAH / diethyl ether / 0 °C 5: 41 percent / AgNO3 / acetone; H2O / 24 h / 40 °C View Scheme