1: 82 percent / dimethylformamide / 1.5 h / Heating 2: 78 percent / Ti(OiPr)4, (+)-DIPT, t-BuOOH / CH2Cl2 / -40 °C 3: 100 percent / hydrazine / 72 h / Ambient temperature 4: 85 percent / K2CO3 / tetrahydrofuran; H2O / 12 h 5: 52 percent / RuCl3, NaIO4, H2O / acetonitrile; CCl4 / 2 h / 20 °C View Scheme

1: 82 percent / dimethylformamide / 1.5 h / Heating 2: 78 percent / Ti(OiPr)4, (+)-DIPT, t-BuOOH / CH2Cl2 / -40 °C 3: 100 percent / hydrazine / 72 h / Ambient temperature 4: 85 percent / K2CO3 / tetrahydrofuran; H2O / 12 h 5: 52 percent / RuCl3, NaIO4, H2O / acetonitrile; CCl4 / 2 h / 20 °C View Scheme

1: pyridine / dichloromethane / 0 - 20 °C 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 3: tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine / tetrahydrofuran / 48 h / 20 °C / |Schlenk technique; |Inert atmosphere View Scheme

With  diisobutylaluminium hydride in  tetrahydrofuran; hexane T=-78 - -30°C;  Inert atmosphere;   

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