1: With diethyl methoxy borane in tetrahydrofuran; methanol T=-78°C; 0.5 h; 2: With sodium tetrahydroborate in tetrahydrofuran; methanol 3 h;

chloro-trimethyl-silane in N,N-dimethyl-formamide T=20°C; 3 h;

1: With diethyl methoxy borane in tetrahydrofuran; methanol T=-78°C; 0.583333 h; 2: With sodium tetrahydroborate in tetrahydrofuran; methanol T=-78°C; 3 - 4 h; 3: With acetic acid in tetrahydrofuran; methanol; water; ethyl acetate T=-78 - 28°C; 0.166667 h;

1: 71.3 percent / acetonitrile / 14 h / Heating 2: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature 3: 1.) Et2BOMe, 2.) NaBH4 / 1.) THF, MeOH, -78 deg C, 30 min, 2.) THF, MeOH, 3 h View Scheme

1: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature 2: 1.) Et2BOMe, 2.) NaBH4 / 1.) THF, MeOH, -78 deg C, 30 min, 2.) THF, MeOH, 3 h View Scheme

1: 86.7 percent / piperidine, AcOH / benzene / Heating 2: 1.) HMPA, 2.) DDQ / 1.) 100 deg C, 22 h, 2.) benzene, 30 min 3: 95.7 percent / m-CPBA / CHCl3 / Ambient temperature 4: 46.9 g / ethanol / 1 h / Ambient temperature 5: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 6: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 7: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 8: 71.3 percent / acetonitrile / 14 h / Heating 9: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature 10: 1.) Et2BOMe, 2.) NaBH4 / 1.) THF, MeOH, -78 deg C, 30 min, 2.) THF, MeOH, 3 h View Scheme

1: 1.) HMPA, 2.) DDQ / 1.) 100 deg C, 22 h, 2.) benzene, 30 min 2: 95.7 percent / m-CPBA / CHCl3 / Ambient temperature 3: 46.9 g / ethanol / 1 h / Ambient temperature 4: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 5: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 6: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 7: 71.3 percent / acetonitrile / 14 h / Heating 8: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature 9: 1.) Et2BOMe, 2.) NaBH4 / 1.) THF, MeOH, -78 deg C, 30 min, 2.) THF, MeOH, 3 h View Scheme

1: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 2: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 3: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 4: 71.3 percent / acetonitrile / 14 h / Heating 5: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature 6: 1.) Et2BOMe, 2.) NaBH4 / 1.) THF, MeOH, -78 deg C, 30 min, 2.) THF, MeOH, 3 h View Scheme

1: 95.7 percent / m-CPBA / CHCl3 / Ambient temperature 2: 46.9 g / ethanol / 1 h / Ambient temperature 3: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 4: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 5: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 6: 71.3 percent / acetonitrile / 14 h / Heating 7: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature 8: 1.) Et2BOMe, 2.) NaBH4 / 1.) THF, MeOH, -78 deg C, 30 min, 2.) THF, MeOH, 3 h View Scheme

1: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 2: 71.3 percent / acetonitrile / 14 h / Heating 3: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature 4: 1.) Et2BOMe, 2.) NaBH4 / 1.) THF, MeOH, -78 deg C, 30 min, 2.) THF, MeOH, 3 h View Scheme