tetrabutyl ammonium fluoride in tetrahydrofuran 0.5 h; Ambient temperature;

triethylamine trihydrofluoride in tetrahydrofuran Ambient temperature;

1: 1.) LiHMDS, 2.) TMSCl / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h; room temperature, 2 h, 3.) -78 deg C, 3 h; -78 deg C to room temperature, 30 min 2: 98 percent / DIBAL-H / toluene / 1.5 h / -78 °C 3: 98 percent / Et3N, DMAP / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) room temperature, 12 h 4: 100 percent / TMSOTf / 1,2-dichloro-ethane / 1.) 0 deg C, 30 min, 2.) room temperature, 90 min 5: 100 percent / AIBN, Bu3SnH / benzene / 1.5 h / Heating 6: 78 percent / triethylamine trihydrofluoride / tetrahydrofuran / Ambient temperature View Scheme

1: With sodium tetrahydroborate in ethanol; dichloromethane Reduction; 2: With ammonia in methanol Deacetylation;

1: 100 percent / AIBN, Bu3SnH / benzene / 1.5 h / Heating 2: 78 percent / triethylamine trihydrofluoride / tetrahydrofuran / Ambient temperature View Scheme

1: 4-chlorophenyl phosphorodichloridate / pyridine / 0 - 5 deg C, 2 h; RT, overnight 2: aq. NH3; dioxane / 2 h / Ambient temperature 3: 85 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

1: aq. NH3; dioxane / 2 h / Ambient temperature 2: 85 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme

1.1: DCC; DMAP / CH2Cl2 2.1: BH3*THF; 2,3-dimethyl-2-butene / tetrahydrofuran 3.1: pyridine; DMAP / CH2Cl2 4.1: iodotrimethylsilane; 2,6-lutidine / CH2Cl2 5.1: NaBH4 / ethanol; CH2Cl2 5.2: 51 percent / NH3(g) / methanol View Scheme

1.1: pyridine; DMAP / CH2Cl2 2.1: iodotrimethylsilane; 2,6-lutidine / CH2Cl2 3.1: NaBH4 / ethanol; CH2Cl2 3.2: 51 percent / NH3(g) / methanol View Scheme

1.1: BH3*THF; 2,3-dimethyl-2-butene / tetrahydrofuran 2.1: pyridine; DMAP / CH2Cl2 3.1: iodotrimethylsilane; 2,6-lutidine / CH2Cl2 4.1: NaBH4 / ethanol; CH2Cl2 4.2: 51 percent / NH3(g) / methanol View Scheme