tetrabutyl ammonium fluoride in tetrahydrofuran 1 h; Ambient temperature;

formic acid 0.05 h;

1: 95 percent / DMAP / dimethylformamide / 3 h / -30 °C 2: 92 percent / BSA / CH2Cl2 / 1.) room temperature, 1 h, 2.) reflux, 5 d 3: 90 percent / NH3 / methanol / 24 h / Ambient temperature 4: 94 percent / pyridine / 1.) 0 deg C, 1 h, 2.) room temperature, 4 h 5: 82 percent / dimethylformamide / 4.5 h / Ambient temperature 6: 82.2 percent / n-Bu3SnH, AIBN / toluene / 1 h / Heating 7: 85 percent / n-Bu4NF / tetrahydrofuran / 1 h / Ambient temperature View Scheme

sodium tris(acetoxy)borohydride; acetic acid in acetonitrile T=0°C; diastereoselective reaction;

1: 82 percent / dimethylformamide / 4.5 h / Ambient temperature 2: 82.2 percent / n-Bu3SnH, AIBN / toluene / 1 h / Heating 3: 85 percent / n-Bu4NF / tetrahydrofuran / 1 h / Ambient temperature View Scheme

1: 82.2 percent / n-Bu3SnH, AIBN / toluene / 1 h / Heating 2: 85 percent / n-Bu4NF / tetrahydrofuran / 1 h / Ambient temperature View Scheme

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in toluene 1 h; Heating;

2: 48 percent / LiCl / dimethylformamide / 6 h / Ambient temperature 3: 60 percent / water / 24 h / Ambient temperature; Dowex-50(H+) 4: n-Bu3SnH, 2,2'-azobis(2-methylpropionitrile) / toluene / 1 h / Heating View Scheme

1: 82 percent / pyridine, water / 3.5 h / Heating 3: 48 percent / LiCl / dimethylformamide / 6 h / Ambient temperature 4: 60 percent / water / 24 h / Ambient temperature; Dowex-50(H+) 5: n-Bu3SnH, 2,2'-azobis(2-methylpropionitrile) / toluene / 1 h / Heating View Scheme

1: 60 percent / water / 24 h / Ambient temperature; Dowex-50(H+) 2: n-Bu3SnH, 2,2'-azobis(2-methylpropionitrile) / toluene / 1 h / Heating View Scheme