1: Ac2O / p-TsOH*H2O / 1.5 h / 25 °C 2: 78 percent / KF / 18-crown-6 / tetrahydrofuran / 1 h / 2 °C 3: 28percent aq. NH4OH / aq. ethanol / 0.5 h / 25 °C 4: CSA / CH2Cl2 / 1 h / 25 °C 5: n-Bu3SnH, AIBN / toluene / 0.33 h / 110 °C 6: 10percent aq. AcOH / acetone / 14 h / 25 °C 7: 5percent NaOMe / methanol / 2 h / 25 °C 8: Na / liquid ammonia / 0.5 h / -78 °C View Scheme

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

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

1: CSA / CH2Cl2 / 1 h / 25 °C 2: n-Bu3SnH, AIBN / toluene / 0.33 h / 110 °C 3: 10percent aq. AcOH / acetone / 14 h / 25 °C 4: 5percent NaOMe / methanol / 2 h / 25 °C 5: Na / liquid ammonia / 0.5 h / -78 °C View Scheme

1: 28percent aq. NH4OH / aq. ethanol / 0.5 h / 25 °C 2: CSA / CH2Cl2 / 1 h / 25 °C 3: n-Bu3SnH, AIBN / toluene / 0.33 h / 110 °C 4: 10percent aq. AcOH / acetone / 14 h / 25 °C 5: 5percent NaOMe / methanol / 2 h / 25 °C 6: Na / liquid ammonia / 0.5 h / -78 °C View Scheme

1: 78 percent / KF / 18-crown-6 / tetrahydrofuran / 1 h / 2 °C 2: 28percent aq. NH4OH / aq. ethanol / 0.5 h / 25 °C 3: CSA / CH2Cl2 / 1 h / 25 °C 4: n-Bu3SnH, AIBN / toluene / 0.33 h / 110 °C 5: 10percent aq. AcOH / acetone / 14 h / 25 °C 6: 5percent NaOMe / methanol / 2 h / 25 °C 7: Na / liquid ammonia / 0.5 h / -78 °C View Scheme

1: NaOH / tetrahydrofuran; H2O 2: OsO4, trimethylamine N-oxide 3: NH3 View Scheme

ammonia T=70°C; P=17251.4 Torr; 24 h; Yield given;

1: 3.20 g / (COCl)2, DMSO / CH2Cl2 / 1 h / -78 °C 2: NaBH4 / ethanol; H2O / 1.5 h / 2 °C 3: 1) NaH / 1) DMF, 25 deg C, 30 min, 2) 25 deg C, 1.5 h 4: 2.85 g / aq. AcOH / 24 h / 25 °C 5: pyridine / CH2Cl2 / 1 h / 2 °C 6: 770 mg / (COCl)2, DMSO / CH2Cl2 / 1 h / -78 °C 7: 90 percent / KF, 18-crown-6 / dimethylformamide / 3 h / 25 °C 8: p-TsOH*H2O / 3 h / 25 °C 9: NaBH4 / ethanol; H2O / 2 h / 25 °C 10: 82 percent / aq. AcOH / 15 h / 80 °C 11: Pb(OAc)4 / benzene / 0.67 h / 25 °C 12: KF, 18-crown-6 / dimethylformamide / 3.5 h / 2 °C 13: 31 percent / Ac2O, p-TsOH*H2O / 1.5 h / 25 °C 14: 78 percent / KF, 18-crown-6 / tetrahydrofuran / 1 h / 2 °C 15: aq. NH4OH / ethanol / 0.5 h / 25 °C 16: d-camphorsulfonic acid / CH2Cl2 / 1 h / 25 °C 17: n-Bu3SnH, AIBN / toluene / 0.33 h / 110 °C 18: aq. AcOH / acetone / 14 h / 35 °C 19: 1) NaOMe, 2) Na, liq. NH3 / 1) MeOH, 25 deg C, 2 h, 2) THF, -78 deg C, 30 min View Scheme

1: NH3 / methanol 2: aq. HCl / methanol View Scheme