1: 1.) OsO4, K3Fe(CN)6, K2CO3, 2.) Na2SO3 / 1.) aq. t-BuOH, 20 deg C 2: 89 percent / H2 / Pd(OH)2/C / ethyl acetate / 20 °C / 4560 Torr 3: 1.) DIBAL-H, 2.) HCl/MeOH / 1.) CH2Cl2, -78 deg C View Scheme

1.1: tetrafluoroboric acid; 3-chloro-benzenecarboperoxoic acid / dichloromethane; water / 48 h / 20 °C 1.2: 48 h / 20 °C / 3800.26 Torr 2.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C 2.2: 16 h / 20 °C View Scheme