1: With bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride in dichloromethane T=20°C; 4 h; 2: With pyridinium chlorochromate in dichloromethane 12 h;

1: Grubbs catalyst / CH2Cl2 2: PCC / CH2Cl2 3: 80 percent / CuBr*Me2S; TMSCl; HMPA / tetrahydrofuran / -78 - 0 °C 4: 98 percent / LiAlH4 / tetrahydrofuran / 3 h / 20 °C 5: DIAD; Ph3P / tetrahydrofuran / 0 - 20 °C 6: NaIO4; OsO4 / methanol; H2O / 3 h / 0 - 20 °C 7: 2.09 g / NaBH4 / methanol / 1 h / 0 °C 8: 91 percent / NH3 / methanol / 24 h / 100 °C 9: 95 percent / aq. HCl / methanol / 3 h / 20 °C View Scheme

1.1: Grubbs catalyst / CH2Cl2 / 4 h / 23 °C 1.2: 87 percent / pyridinium chlorochromate / CH2Cl2 / 12 h / 23 °C 2.1: 95 percent / hydrogen / Pd/C / ethyl acetate / 20 °C View Scheme