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 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 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 View Scheme

1: 46.9 g / ethanol / 1 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h View Scheme

sodium hydride 1.) DMF, 30 min, 2.) DMF, RT, 2 h; Yield given. Multistep reaction;

1: diisobutylaluminium hydride / toluene / -78 - 0 °C / Inert atmosphere 2: triethylamine; methanesulfonyl chloride / dichloromethane / 5 h / 0 - 25 °C 3: hydrogen bromide / water / 15 h / 80 °C 4: toluene / 3 h / 0 - 20 °C 5: potassium carbonate / N,N-dimethyl-formamide / 6 h / 70 - 75 °C 6: sulfuric acid / acetonitrile / 3 h / 50 - 60 °C View Scheme

1: diisobutylaluminium hydride / toluene / -78 - 0 °C / Inert atmosphere 2: triethylamine; methanesulfonyl chloride / dichloromethane / 5 h / 0 - 25 °C 3: hydrogen bromide / water / 15 h / 80 °C View Scheme

1: diisobutylaluminium hydride / toluene / -78 - 0 °C / Inert atmosphere 2: triethylamine; methanesulfonyl chloride / dichloromethane / 5 h / 0 - 25 °C 3: hydrogen bromide / water / 15 h / 80 °C 4: 9 h / 90 - 100 °C View Scheme

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

1: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 2: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 3: 71.3 percent / acetonitrile / 14 h / Heating 4: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature View Scheme