1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether View Scheme

1: 1) NaH / 1) THF, 1 h, reflux, 2) 1 h, reflux 2: 97 percent / 14percent aq. HIO4, AcOH / 0.67 h / 15 °C View Scheme

1: pyridine 2: NaN3, 15-crown-5 3: LiAlH4 / diethyl ether 4: Na2CO3 View Scheme

1: 93 percent / NaH / dimethylformamide 2: 73 percent / 0.1 M aq. HCl / methanol / 6 h / 20 °C 3: 1.) sodium metaperiodate, 2.) NaBH4 / 1.) H2O, 20 deg C, 1 h, 2.) H2O, 20 deg C, 4 h 4: potassium tert-butoxide / dimethylsulfoxide / 50 °C 5: pyridine 6: HgCl2, HgO / acetone View Scheme

1: NaH / dimethylformamide / 1.5 h / 25 °C 2: 80percent aq. AcOH / 24 h / 25 °C 3: pyridine / CH2Cl2 / 1 h / 2 °C 4: (COCl)2, DMSO, Et3N / CH2Cl2 / 1 h / -78 °C 5: 90 percent / KF / 18-crown-6 / dimethylformamide / 3 h / 25 °C 6: p-TsOH*H2O / 3 h / 25 °C 7: NaBH4 / aq. ethanol / 2 h / 25 °C 8: 82 percent / 80percent aq. AcOH / 15 h / 80 °C 9: Pb(OAc)4 / benzene / 0.67 h / 25 °C 10: KF / 18-crown-6 / dimethylformamide / 3.5 h / 2 °C 11: Ac2O / p-TsOH*H2O / 1.5 h / 25 °C 12: 78 percent / KF / 18-crown-6 / tetrahydrofuran / 1 h / 2 °C 13: 28percent aq. NH4OH / aq. ethanol / 0.5 h / 25 °C 14: CSA / CH2Cl2 / 1 h / 25 °C 15: n-Bu3SnH, AIBN / toluene / 0.33 h / 110 °C 16: 10percent aq. AcOH / acetone / 14 h / 25 °C 17: 5percent NaOMe / methanol / 2 h / 25 °C 18: Na / liquid ammonia / 0.5 h / -78 °C View Scheme