1: OsO4, NaIO4 / diethyl ether; H2O 2: LAH / diethyl ether 3: 1.) pyridine; 2.) 6N HCl aq. View Scheme

Yield given. Multistep reaction;

1: LiAlH4 / diethyl ether / 1 h / below 10 deg C 2: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating 3: OsO4, NaIO4 / diethyl ether; H2O / 7 h 4: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C 5: pyridine / Ambient temperature 6: 75 percent AcOH / 1 h / 30 °C 7: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min 8: NaOAc / 0.67 h / 130 °C 9: 1 percent NaOMe / methanol / 1 h / Ambient temperature 10: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C 11: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h 12: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature 13: 84 percent / TMSCl, NaI / acetonitrile / -10 °C 14: 86 percent / sodium naphtalenide / 0.08 h / -70 °C 15: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature 16: 1.) hexamethyldisilazane, n-BuLi / 1.) THF, n-hexane, -10 deg C, 10 min; 2.) THF, -70 deg C, 1 h; 3.) THF, -5 to 20 deg C, 5 min View Scheme