1: (i) LiNH2, liq. NH3, (ii) aq. HCl 2: (i) CrO3, H2SO4, (ii) /BRN= 1098229/, HCl 3: H2, quinoline / Pd-BaSO4 4: (i) NaOEt, (ii) aq. HCl 5: (microbiological transformation) 6: (i) Et3N, (ii) Al, (iii) AcOH View Scheme

1: (i) CrO3, H2SO4, (ii) /BRN= 1098229/, HCl 2: H2, quinoline / Pd-BaSO4 3: (i) NaOEt, (ii) aq. HCl 4: (microbiological transformation) 5: (i) Et3N, (ii) Al, (iii) AcOH View Scheme

1: H2, quinoline / Pd-BaSO4 2: (i) NaOEt, (ii) aq. HCl 3: (microbiological transformation) 4: (i) Et3N, (ii) Al, (iii) AcOH View Scheme

1: H2 / Lindlar's catalyst / ethyl acetate 2: camphorsulfonic acid / methanol 3: CBr4, triphenylphosphine / acetonitrile 4: NaI / acetone View Scheme

1: NaH / tetrahydrofuran / 2 h / 0 °C 2: AcOH / methanol / 6 h / 40 °C 3: imidazole / dimethylformamide / 10 h / Ambient temperature 4: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 5: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 6: NaOCl / CH2Cl2 / 4 h / Ambient temperature 7: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 8: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 9: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 10: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 11: CrO3, H+ 13: Bu4NF View Scheme

1: AcOH / methanol / 6 h / 40 °C 2: imidazole / dimethylformamide / 10 h / Ambient temperature 3: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 4: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 5: NaOCl / CH2Cl2 / 4 h / Ambient temperature 6: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 7: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 8: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 9: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 10: CrO3, H+ 12: Bu4NF View Scheme

1: diisobutylaluminum hydride (Dibal) / hexane; diethyl ether / 0.5 h / -20 °C 2: NH2OH*HCl, pyridine / CH2Cl2 / 4 h / Ambient temperature 3: NaOCl / CH2Cl2 / 4 h / Ambient temperature 4: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 5: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 6: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 7: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 8: CrO3, H+ 10: Bu4NF View Scheme

1: NaOCl / CH2Cl2 / 4 h / Ambient temperature 2: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 3: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 4: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 5: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 6: CrO3, H+ 8: Bu4NF View Scheme

1: H2, B(OH)3 / 10percent Pd/C / tetrahydrofuran; H2O / 4 h / 760 Torr / Ambient temperature 2: CH3SO2Cl, Et3N / CH2Cl2 / 0.67 h / 0 °C 3: 1.) CuCN / 2.) THF, from -78 deg C to 0 deg C, 1 h 4: pyridinium p-toluenesulfonate (PPTS) / methanol; diethyl ether 5: CrO3, H+ 7: Bu4NF View Scheme

anhydrous guanidine in methanol T=0°C;