1: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating 2: OsO4, NaIO4 / diethyl ether; H2O 3: LAH / diethyl ether 4: 1.) pyridine; 2.) 6N HCl aq. View Scheme

1: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating 2: LiAlH4 / diethyl ether / 1 h / below 10 deg C 3: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating 4: OsO4, NaIO4 / diethyl ether; H2O / 7 h 5: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C 6: pyridine / Ambient temperature 7: 75 percent AcOH / 1 h / 30 °C 8: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min 9: NaOAc / 0.67 h / 130 °C 10: 1 percent NaOMe / methanol / 1 h / Ambient temperature 11: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C 12: 1.) NaN(TMS)2; 2.) LiAlH4 / 1.) DME, 50 min, reflux; 2.) Et2O, 0 deg C, 1 h 13: DMAP, pyridine / tetrahydrofuran / 24 h / Ambient temperature 14: 84 percent / TMSCl, NaI / acetonitrile / -10 °C 15: 86 percent / sodium naphtalenide / 0.08 h / -70 °C 16: 69 percent / PCC, molecular sieves 3A / CH2Cl2 / 0.5 h / Ambient temperature 17: 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

Multi-step reaction with 2 steps 1: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating2: OsO4, NaIO4 / diethyl ether; H2O  

Multi-step reaction with 7 steps 1: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating2: LiAlH4 / diethyl ether / 1 h / below 10 deg C3: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating4: OsO4, NaIO4 / diethyl ether; H2O / 7 h5: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C6: pyridine / Ambient temperature7: 75 percent AcOH / 1 h / 30 °C  

Multi-step reaction with 11 steps 1: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating2: LiAlH4 / diethyl ether / 1 h / below 10 deg C3: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating4: OsO4, NaIO4 / diethyl ether; H2O / 7 h5: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C6: pyridine / Ambient temperature7: 75 percent AcOH / 1 h / 30 °C8: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min9: NaOAc / 0.67 h / 130 °C10: 1 percent NaOMe / methanol / 1 h / Ambient temperature11: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C  

Multi-step reaction with 10 steps 1: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating2: LiAlH4 / diethyl ether / 1 h / below 10 deg C3: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating4: OsO4, NaIO4 / diethyl ether; H2O / 7 h5: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C6: pyridine / Ambient temperature7: 75 percent AcOH / 1 h / 30 °C8: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min9: NaOAc / 0.67 h / 130 °C10: 1 percent NaOMe / methanol / 1 h / Ambient temperature  

Multi-step reaction with 12 steps 1: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating2: LiAlH4 / diethyl ether / 1 h / below 10 deg C3: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating4: OsO4, NaIO4 / diethyl ether; H2O / 7 h5: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C6: pyridine / Ambient temperature7: 75 percent AcOH / 1 h / 30 °C8: 1.) LDA / 1.) THF, below -60 deg C, 20 min; 2.) THF, below -60 deg C, 30 min9: NaOAc / 0.67 h / 130 °C10: 1 percent NaOMe / methanol / 1 h / Ambient temperature11: 97 percent / Et3N, DMAP / CH2Cl2 / 7 h / below 0 deg C12: NaN(TMS)2 / 1,2-dimethoxy-ethane / 0.83 h / Heating  

Multi-step reaction with 2 steps 1: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating2: LiAlH4 / diethyl ether / 1 h / below 10 deg C  

Multi-step reaction with 5 steps 1: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating2: LiAlH4 / diethyl ether / 1 h / below 10 deg C3: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating4: OsO4, NaIO4 / diethyl ether; H2O / 7 h5: LiAlH4 / diethyl ether / 0.5 h / below 10 deg C  

Multi-step reaction with 4 steps 1: 62 percent / 1.) KOH / methanol; H2O / 2 h / Heating2: LiAlH4 / diethyl ether / 1 h / below 10 deg C3: EtN(i-Pr)2 / CH2Cl2 / 24 h / Heating4: OsO4, NaIO4 / diethyl ether; H2O / 7 h