1: 100 percent / H2 / Pd/C / methanol 2: 82 percent / Fremy's salt / acetone; H2O 3: 1.) TFA, 2.) NaHCO3 / 1.) CH2Cl2, 2.) EtOH 4: CuCl2, Et3N, O2 / acetonitrile 5: NaOMe / methanol View Scheme

1: iron dust, 12 M HCl / methanol / 10 h / Heating 2: Na2CO3 / diethyl ether; H2O / 1.) 0 deg C, 30 min; 2.) room temp., 2 h 3: 93 percent / Jones reagent / acetone / 1.) 0 deg C, 30 min; 2.) room temp., 1 h 4: tetrahydrofuran / 2 h / Ambient temperature 5: 2 M aq. NaN3 / tetrahydrofuran; H2O / 2 h / Ambient temperature 6: toluene / 0.5 h / Heating 7: toluene / 2 h / 60 °C 8: 100 percent / hydrogen / 10percent Pd-C / ethanol / 2 h 9: acetonitrile / 1 h 10: NaBH3CN / acetonitrile / 12 h / 50 °C 11: 85 percent / molecular sieves 3 Angstroem / ethanol / 72 h / Heating 12: hydrogen, 60percent HClO4 / Pd-black / acetic acid / 20 h / Ambient temperature 13: 5 M KOH / methanol / 3 h / Ambient temperature 14: DCC / tetrahydrofuran 15: BH3*SMe2 / tetrahydrofuran / 3 h / Ambient temperature 16: CAN / acetonitrile; H2O / 0.08 h / Ambient temperature 17: 74 percent / Na2CO3 / ethanol / 3 h / Ambient temperature 18: 24 percent / LiClO4 / acetonitrile / 1 h / electrolysis View Scheme

1: acetonitrile / 1 h 2: NaBH3CN / acetonitrile / 12 h / 50 °C 3: 85 percent / molecular sieves 3 Angstroem / ethanol / 72 h / Heating 4: hydrogen, 60percent HClO4 / Pd-black / acetic acid / 20 h / Ambient temperature 5: 5 M KOH / methanol / 3 h / Ambient temperature 6: DCC / tetrahydrofuran 7: BH3*SMe2 / tetrahydrofuran / 3 h / Ambient temperature 8: CAN / acetonitrile; H2O / 0.08 h / Ambient temperature 9: 74 percent / Na2CO3 / ethanol / 3 h / Ambient temperature 10: 24 percent / LiClO4 / acetonitrile / 1 h / electrolysis View Scheme

1: tetrahydrofuran / 2 h / Ambient temperature 2: 2 M aq. NaN3 / tetrahydrofuran; H2O / 2 h / Ambient temperature 3: toluene / 0.5 h / Heating 4: toluene / 2 h / 60 °C 5: 100 percent / hydrogen / 10percent Pd-C / ethanol / 2 h 6: acetonitrile / 1 h 7: NaBH3CN / acetonitrile / 12 h / 50 °C 8: 85 percent / molecular sieves 3 Angstroem / ethanol / 72 h / Heating 9: hydrogen, 60percent HClO4 / Pd-black / acetic acid / 20 h / Ambient temperature 10: 5 M KOH / methanol / 3 h / Ambient temperature 11: DCC / tetrahydrofuran 12: BH3*SMe2 / tetrahydrofuran / 3 h / Ambient temperature 13: CAN / acetonitrile; H2O / 0.08 h / Ambient temperature 14: 74 percent / Na2CO3 / ethanol / 3 h / Ambient temperature 15: 24 percent / LiClO4 / acetonitrile / 1 h / electrolysis View Scheme

1: 85 percent / molecular sieves 3 Angstroem / ethanol / 72 h / Heating 2: hydrogen, 60percent HClO4 / Pd-black / acetic acid / 20 h / Ambient temperature 3: 5 M KOH / methanol / 3 h / Ambient temperature 4: DCC / tetrahydrofuran 5: BH3*SMe2 / tetrahydrofuran / 3 h / Ambient temperature 6: CAN / acetonitrile; H2O / 0.08 h / Ambient temperature 7: 74 percent / Na2CO3 / ethanol / 3 h / Ambient temperature 8: 24 percent / LiClO4 / acetonitrile / 1 h / electrolysis View Scheme

1: 100 percent / hydrogen / 10percent Pd-C / ethanol / 2 h 2: acetonitrile / 1 h 3: NaBH3CN / acetonitrile / 12 h / 50 °C 4: 85 percent / molecular sieves 3 Angstroem / ethanol / 72 h / Heating 5: hydrogen, 60percent HClO4 / Pd-black / acetic acid / 20 h / Ambient temperature 6: 5 M KOH / methanol / 3 h / Ambient temperature 7: DCC / tetrahydrofuran 8: BH3*SMe2 / tetrahydrofuran / 3 h / Ambient temperature 9: CAN / acetonitrile; H2O / 0.08 h / Ambient temperature 10: 74 percent / Na2CO3 / ethanol / 3 h / Ambient temperature 11: 24 percent / LiClO4 / acetonitrile / 1 h / electrolysis View Scheme

1: hydrogen, 60percent HClO4 / Pd-black / acetic acid / 20 h / Ambient temperature 2: 5 M KOH / methanol / 3 h / Ambient temperature 3: DCC / tetrahydrofuran 4: BH3*SMe2 / tetrahydrofuran / 3 h / Ambient temperature 5: CAN / acetonitrile; H2O / 0.08 h / Ambient temperature 6: 74 percent / Na2CO3 / ethanol / 3 h / Ambient temperature 7: 24 percent / LiClO4 / acetonitrile / 1 h / electrolysis View Scheme

anodic oxidation;

1: 63 percent / HNO3 / 1.) -50-(-40) deg C, 1 h, 2.) -30 deg C, 25 min 2: 73 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C 3: 93 percent / HCl / diethyl ether / 65 h / Heating 4: 86 percent / NiCl2, BaBH4 / methanol / 0.08 h / 50 °C 5: 64 percent / aq. HCl / tetrahydrofuran / 1 h / 40 °C 6: 51 percent / cerium ammonium nitrate 8: 24 percent / electrochemical oxidation View Scheme

2: 24 percent / electrochemical oxidation View Scheme