1: Grubbs catalyst / CH2Cl2 2: PCC / CH2Cl2 3: 80 percent / CuBr*Me2S; TMSCl; HMPA / tetrahydrofuran / -78 - 0 °C 4: 98 percent / LiAlH4 / tetrahydrofuran / 3 h / 20 °C 5: DIAD; Ph3P / tetrahydrofuran / 0 - 20 °C 6: NaIO4; OsO4 / methanol; H2O / 3 h / 0 - 20 °C 7: 2.09 g / NaBH4 / methanol / 1 h / 0 °C 8: 91 percent / NH3 / methanol / 24 h / 100 °C 9: 95 percent / aq. HCl / methanol / 3 h / 20 °C View Scheme

1: DMAP / pyridine 2: 43 percent / Pd(PPh3)4 / dimethylformamide / 55 °C 3: NaOH / tetrahydrofuran; H2O 4: OsO4, trimethylamine N-oxide 5: NH3 View Scheme

1: 1.) LiAlH4, 2.) NaIO4, 3.) NaBH4 2: DMAP / pyridine 3: 43 percent / Pd(PPh3)4 / dimethylformamide / 55 °C 4: NaOH / tetrahydrofuran; H2O 5: OsO4, trimethylamine N-oxide 6: NH3 View Scheme

1: 43 percent / Pd(PPh3)4 / dimethylformamide / 55 °C 2: NaOH / tetrahydrofuran; H2O 3: OsO4, trimethylamine N-oxide 4: NH3 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

1: NaBH4 / aq. ethanol / 1.5 h / 2 °C 2: NaH / dimethylformamide / 1.5 h / 25 °C 3: 80percent aq. AcOH / 24 h / 25 °C 4: pyridine / CH2Cl2 / 1 h / 2 °C 5: (COCl)2, DMSO, Et3N / CH2Cl2 / 1 h / -78 °C 6: 90 percent / KF / 18-crown-6 / dimethylformamide / 3 h / 25 °C 7: p-TsOH*H2O / 3 h / 25 °C 8: NaBH4 / aq. ethanol / 2 h / 25 °C 9: 82 percent / 80percent aq. AcOH / 15 h / 80 °C 10: Pb(OAc)4 / benzene / 0.67 h / 25 °C 11: KF / 18-crown-6 / dimethylformamide / 3.5 h / 2 °C 12: Ac2O / p-TsOH*H2O / 1.5 h / 25 °C 13: 78 percent / KF / 18-crown-6 / tetrahydrofuran / 1 h / 2 °C 14: 28percent aq. NH4OH / aq. ethanol / 0.5 h / 25 °C 15: CSA / CH2Cl2 / 1 h / 25 °C 16: n-Bu3SnH, AIBN / toluene / 0.33 h / 110 °C 17: 10percent aq. AcOH / acetone / 14 h / 25 °C 18: 5percent NaOMe / methanol / 2 h / 25 °C 19: Na / liquid ammonia / 0.5 h / -78 °C View Scheme

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

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

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

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