1: 58 percent / LAH / diethyl ether / 6 h / -78 °C 2: 93 percent / m-CPBA (80 percent) / CH2Cl2 / 0.67 h / 0 °C 3: 97 percent / H2, 1M NaOH / 10percent Pd/C / ethanol / 6 h / -60 °C 4: 89 percent / LiBr, NCS / methanol / 1 h / Ambient temperature 5: 79 percent / TsOH / 5 h / Ambient temperature 6: 1.) t-BuLi / 1.) Et2O, hexane, -78 deg C, 1.75 h, 2.) Et2O, hexane, RT 7: 93 percent / H2O, 5percent HCl / methanol / RT, 8 h, then -20 deg C, 16 h 8: 72 percent / RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / 1.25 h / Ambient temperature View Scheme

1: 58 percent / LAH / diethyl ether / 6 h / -78 °C 2: 1.) (L)-(+)-diisopropyl tartrate, 4A sieves, Ti(OiPr)4, t-BuOOH / 1.) CH2Cl2, 1 h, 2.) CH2Cl2, -20 deg C, 3.5 h 3: H2, 1M NaOH / 10percent Pd/C / ethanol / Ambient temperature 4: LiBr, NCS / methanol / Ambient temperature 5: TsOH / Ambient temperature 6: 1.) t-BuLi / 1.) Et2O, hexane, -78 deg C, 2.) Et2O, hexane, RT 7: H2O, 5percent HCl / methanol / RT, then -20 deg C 8: RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / Ambient temperature View Scheme

1: 58 percent / LAH / diethyl ether / 6 h / -78 °C 2: 93 percent / m-CPBA (80 percent) / CH2Cl2 / 0.67 h / 0 °C 3: 97 percent / H2, 1M NaOH / 10percent Pd/C / ethanol / 6 h / -60 °C 4: 98 percent / ICl / CH2Cl2 / Ambient temperature 5: RuCl3*H2O, NaIO4 / CCl4; acetonitrile; H2O / Ambient temperature 6: 1.) ZnCl2, 2.) dichlorobis(triphenylphosphine)palladium(II), DIBALH / 1.) ether, THF, RT, 10 min, 2.) ether, THF, RT, 1.5 h View Scheme