1: 85 percent / K2CO3 / tetrahydrofuran; H2O / 12 h 2: 52 percent / RuCl3, NaIO4, H2O / acetonitrile; CCl4 / 2 h / 20 °C View Scheme

1: 85 percent / K2CO3 / tetrahydrofuran; H2O / 12 h 2: 52 percent / RuCl3, NaIO4, H2O / acetonitrile; CCl4 / 2 h / 20 °C View Scheme

toluene-4-sulfonic acid in isopropyl alcohol 1 h; Reflux;

Multi-step reaction with 4 steps 1: 86 percent / DIBAL-H / toluene / 2 h / 0 °C2: 82 percent / dimethylformamide / 1.5 h / Heating3: 78 percent / Ti(OiPr)4, (+)-DIPT, t-BuOOH / CH2Cl2 / -40 °C4: 100 percent / hydrazine / 72 h / Ambient temperature  

Multi-step reaction with 3 steps 1: 82 percent / dimethylformamide / 1.5 h / Heating2: 78 percent / Ti(OiPr)4, (+)-DIPT, t-BuOOH / CH2Cl2 / -40 °C3: 100 percent / hydrazine / 72 h / Ambient temperature