W-6 Raney Ni in methanol 6 h; Heating;

1.1: i-Pr2NH; BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C 1.2: 54 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 19 h 2.1: m-CPBA / CH2Cl2 / 0.5 h / 0 °C 3.1: 0.191 g / toluene / 1 h / Heating 4.1: 89 percent / HF*pyridine / tetrahydrofuran / 25 h / 20 °C 5.1: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 6.1: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 7.1: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme

1.1: NaHMDS / tetrahydrofuran; toluene / 0.5 h / 0 °C 1.2: 89 percent / tetrahydrofuran; toluene; hexamethylphosphoric acid triamide / 6 h / 0 - 20 °C 2.1: 96 percent / p-TsOH*H2O / methanol / 8 h / 20 °C 3.1: mCPBA / 1,2-dichloro-ethane / 0.25 h / 0 °C 4.1: 720 mg / toluene / 0.5 h / Heating 5.1: 95 percent / Dess-Martin periodinane / 1,2-dichloro-ethane / 0.25 h / 20 °C 6.1: 85 percent / CrCl2 / tetrahydrofuran / 8 h / 20 °C 7.1: 66 percent / Et3N; CuI / Pd(PPh3)4 / benzene; tetrahydrofuran / 2 h / 20 °C 8.1: H2 / Rh(PPh3)3Cl / benzene / 8 h 9.1: 1.0 mg / Me2S; BF3*Et2O / 0.08 h / 0 °C View Scheme