1: tetrahydrofuran; diethyl ether / 3 h / 20 °C 2: 32 mg / trifluoroacetic acid / Pd/C / 3 h / 20 °C View Scheme

1: 75 percent / n-Bu3SnH; AIBN / benzene / 3 h / Heating 2: tetrahydrofuran; diethyl ether / 3 h / 20 °C 3: 32 mg / trifluoroacetic acid / Pd/C / 3 h / 20 °C View Scheme

1: iodine / THF 2: 2.) NaBH4 View Scheme

1: 68 percent / potassium hydride, HMPA / tetrahydrofuran / 20 h / Ambient temperature 2: 1.) tert-butyllithium / 1.) THF, r.t., 2 h; 2.) r.t., overnight 3: 72 percent / sodium hydroxide / methanol / 4 h / Heating 4: 89 percent / ethyl acetate / 5 h / 50 °C 6: 54 percent / triphenylphosphine / dimethylformamide / 86 h / Heating 7: 54 percent / tetrahydrofuran / 1.) r.t., 30 min; 2.) reflux, 1 h 8: 2.) NaBH4 / 1.) MeOH, 50 deg C, 5h; 2.) MeOH, 0 deg C, 1h View Scheme

1: 1.) tert-butyllithium / 1.) THF, r.t., 2 h; 2.) r.t., overnight 2: 72 percent / sodium hydroxide / methanol / 4 h / Heating 3: 89 percent / ethyl acetate / 5 h / 50 °C 5: 54 percent / triphenylphosphine / dimethylformamide / 86 h / Heating 6: 54 percent / tetrahydrofuran / 1.) r.t., 30 min; 2.) reflux, 1 h 7: 2.) NaBH4 / 1.) MeOH, 50 deg C, 5h; 2.) MeOH, 0 deg C, 1h View Scheme

sodium tetrahydroborate 1.) MeOH, 50 deg C, 5h; 2.) MeOH, 0 deg C, 1h; Yield given. Multistep reaction;

P=2206.5 Torr; Hydration;

Hydration;