1.1: 61 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 20 °C 2.1: magnesium / tetrahydrofuran / 0.75 h / Heating 2.2: tetrahydrofuran / -16 - -14 °C 2.3: tetrahydrofuran / 1 h 3.1: 0.176 g / 0.25 h 4.1: triethyl amine / CH2Cl2 / 3 h / 20 °C 5.1: 0.110 g / DBU / 12 h / 60 °C 6.1: hydrogen / palladium on charcoal / methanol / 8 h / 65 °C / 10343 Torr 7.1: 0.041 g / HBr / 5 h / Heating View Scheme

1.1: 93 percent / p-TSA / 0.08 h / 0 °C 2.1: 78 percent / DIBAL-H / toluene / 2 h / -78 °C 3.1: 80 percent / DBU / CH2Cl2 / 0.5 h / Heating 4.1: 53 percent / tri-n-butyltin hydride; AIBN / benzene / 4 h / Heating 5.1: 75 percent / BF3*Et2O / CH2Cl2 / 2 h / 20 °C 6.1: 61 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 20 °C 7.1: magnesium / tetrahydrofuran / 0.75 h / Heating 7.2: tetrahydrofuran / -16 - -14 °C 7.3: tetrahydrofuran / 1 h 8.1: 0.176 g / 0.25 h 9.1: triethyl amine / CH2Cl2 / 3 h / 20 °C 10.1: 0.110 g / DBU / 12 h / 60 °C 11.1: hydrogen / palladium on charcoal / methanol / 8 h / 65 °C / 10343 Torr 12.1: 0.041 g / HBr / 5 h / Heating View Scheme

1.1: 78 percent / DIBAL-H / toluene / 2 h / -78 °C 2.1: 80 percent / DBU / CH2Cl2 / 0.5 h / Heating 3.1: 53 percent / tri-n-butyltin hydride; AIBN / benzene / 4 h / Heating 4.1: 75 percent / BF3*Et2O / CH2Cl2 / 2 h / 20 °C 5.1: 61 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 20 °C 6.1: magnesium / tetrahydrofuran / 0.75 h / Heating 6.2: tetrahydrofuran / -16 - -14 °C 6.3: tetrahydrofuran / 1 h 7.1: 0.176 g / 0.25 h 8.1: triethyl amine / CH2Cl2 / 3 h / 20 °C 9.1: 0.110 g / DBU / 12 h / 60 °C 10.1: hydrogen / palladium on charcoal / methanol / 8 h / 65 °C / 10343 Torr 11.1: 0.041 g / HBr / 5 h / Heating View Scheme

1.1: 75 percent / BF3*Et2O / CH2Cl2 / 2 h / 20 °C 2.1: 61 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 20 °C 3.1: magnesium / tetrahydrofuran / 0.75 h / Heating 3.2: tetrahydrofuran / -16 - -14 °C 3.3: tetrahydrofuran / 1 h 4.1: 0.176 g / 0.25 h 5.1: triethyl amine / CH2Cl2 / 3 h / 20 °C 6.1: 0.110 g / DBU / 12 h / 60 °C 7.1: hydrogen / palladium on charcoal / methanol / 8 h / 65 °C / 10343 Torr 8.1: 0.041 g / HBr / 5 h / Heating View Scheme

1: triethyl amine / CH2Cl2 / 3 h / 20 °C 2: 0.110 g / DBU / 12 h / 60 °C 3: hydrogen / palladium on charcoal / methanol / 8 h / 65 °C / 10343 Torr 4: 0.041 g / HBr / 5 h / Heating View Scheme

1: 0.110 g / DBU / 12 h / 60 °C 2: hydrogen / palladium on charcoal / methanol / 8 h / 65 °C / 10343 Torr 3: 0.041 g / HBr / 5 h / Heating View Scheme

1.1: 80 percent / DBU / CH2Cl2 / 0.5 h / Heating 2.1: 53 percent / tri-n-butyltin hydride; AIBN / benzene / 4 h / Heating 3.1: 75 percent / BF3*Et2O / CH2Cl2 / 2 h / 20 °C 4.1: 61 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 20 °C 5.1: magnesium / tetrahydrofuran / 0.75 h / Heating 5.2: tetrahydrofuran / -16 - -14 °C 5.3: tetrahydrofuran / 1 h 6.1: 0.176 g / 0.25 h 7.1: triethyl amine / CH2Cl2 / 3 h / 20 °C 8.1: 0.110 g / DBU / 12 h / 60 °C 9.1: hydrogen / palladium on charcoal / methanol / 8 h / 65 °C / 10343 Torr 10.1: 0.041 g / HBr / 5 h / Heating View Scheme

1.1: 53 percent / tri-n-butyltin hydride; AIBN / benzene / 4 h / Heating 2.1: 75 percent / BF3*Et2O / CH2Cl2 / 2 h / 20 °C 3.1: 61 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 20 °C 4.1: magnesium / tetrahydrofuran / 0.75 h / Heating 4.2: tetrahydrofuran / -16 - -14 °C 4.3: tetrahydrofuran / 1 h 5.1: 0.176 g / 0.25 h 6.1: triethyl amine / CH2Cl2 / 3 h / 20 °C 7.1: 0.110 g / DBU / 12 h / 60 °C 8.1: hydrogen / palladium on charcoal / methanol / 8 h / 65 °C / 10343 Torr 9.1: 0.041 g / HBr / 5 h / Heating View Scheme

1.1: p-TSA / 20 °C 2.1: NaH / dimethylformamide / 6 h / 0 - 20 °C 3.1: 98 percent / p-TSA / tetrahydrofuran; H2O / 6 h / Heating 4.1: NaIO4 / acetone; H2O / 0.5 h / 20 °C 5.1: Et3N; DMAP / 1,2-dichloro-ethane / 4 h / Heating 6.1: 62 percent / BF3*Et2O / CH2Cl2 / 0.25 h / -78 - 20 °C 7.1: NaBH4 / methanol / 4 h / 0 - 20 °C 7.2: 93 percent / TMSCl / 4 h / 40 °C 8.1: NaIO4 / acetone; H2O / 0.5 h / 20 °C 9.1: p-TSA / benzene / 6 h / Heating 10.1: 95 percent / Pd-CaCO3 / methanol / 24 h / 20 °C 11.1: DBU / toluene / 24 h / Heating 12.1: NaBH4 / ethanol / 2 h / Heating 13.1: 74 percent / Et3N; DMAP / 4 h / 0 - 20 °C 14.1: 78 percent / Na2S / dimethylformamide / 2 h / 100 °C 15.1: 82 percent / aq. HCl / acetic acid / 24 h / 20 °C 16.1: 89 percent / CH2Cl2 / 12 h / 20 °C 17.1: 97 percent / aq. NaOH / methanol / 12 h / 0 °C 18.1: 96 percent / H2 / 10percent Pd/C / 8 h / 2280.15 Torr 19.1: 80 percent / 48percent HBr / 2 h / Heating View Scheme

1: DBU / toluene / 24 h / Heating 2: NaBH4 / ethanol / 2 h / Heating 3: 74 percent / Et3N; DMAP / 4 h / 0 - 20 °C 4: 78 percent / Na2S / dimethylformamide / 2 h / 100 °C 5: 82 percent / aq. HCl / acetic acid / 24 h / 20 °C 6: 89 percent / CH2Cl2 / 12 h / 20 °C 7: 97 percent / aq. NaOH / methanol / 12 h / 0 °C 8: 96 percent / H2 / 10percent Pd/C / 8 h / 2280.15 Torr 9: 80 percent / 48percent HBr / 2 h / Heating View Scheme