1: 0.75 g / 1N NaOH, H2 / 5percent Pd/C / H2O / 760 Torr 2: SOCl2, pyridine 4: tetrahydrofuran / a) -78 deg C, 5h, b) -20 deg C, 16h 5: 28percent NaOH / ethanol / Ambient temperature 6: 111 mg / Ce(NH4)2(NO3)6 / acetonitrile; H2O / 0.17 h / Ambient temperature View Scheme

1: 0.75 g / 1N NaOH, H2 / 5percent Pd/C / H2O / 760 Torr 2: SOCl2, pyridine 4: tetrahydrofuran / a) -78 deg C, 5h, b) -20 deg C, 16h 5: 28percent NaOH / ethanol / Ambient temperature 6: 111 mg / Ce(NH4)2(NO3)6 / acetonitrile; H2O / 0.17 h / Ambient temperature View Scheme

1: 0.75 g / 1N NaOH, H2 / 5percent Pd/C / H2O / 760 Torr 2: SOCl2, pyridine 4: tetrahydrofuran / a) -78 deg C, 5h, b) -20 deg C, 16h 5: reducing agent: hydride 6: 95 percent / pyridine / CH2Cl2 / a) 0 deg C, 1h, b) r.t., 16h 7: 105 mg / 1,5N KOH/EtOH / 0.17 h / Ambient temperature 8: CuBr*Me2S / diethyl ether / Ambient temperature; or Cu(I)-pentin-1-ide 9: 480 mg / Ce(NH4)2(NO3)6 / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

1: 0.75 g / 1N NaOH, H2 / 5percent Pd/C / H2O / 760 Torr 2: SOCl2, pyridine 4: tetrahydrofuran / a) -78 deg C, 5h, b) -20 deg C, 16h 5: reducing agent: hydride 6: 95 percent / pyridine / CH2Cl2 / a) 0 deg C, 1h, b) r.t., 16h 7: 105 mg / 1,5N KOH/EtOH / 0.17 h / Ambient temperature 8: CuBr*Me2S / diethyl ether / Ambient temperature; or Cu(I)-pentin-1-ide 9: 480 mg / Ce(NH4)2(NO3)6 / acetonitrile; H2O / 1 h / Ambient temperature 10: 1) H2, 2) conc. HCl / 1) 10percent Pd/C / 1) MeOH, 760 Torr, 2) 50 deg C, 2h View Scheme