1: 1.) NaH 2: 100 percent / aq. KOH / methanol / 5 h / Heating 3: 83 percent / diethyl phosphorocyanidate, Et3N / dimethylformamide / 2 h / 0 °C 4: 100 percent / aq. KOH / methanol / 10 h / Heating 5: 87 percent / NBS / dimethylformamide / 24 h / Ambient temperature 6: 6N aq. HCl / 12 h / Heating 7: diethyl ether 8: 98 percent / K2CO3 / 6 h / Ambient temperature 9: 94 percent / Ph3P, diethylazodicarboxylate / tetrahydrofuran / 2 h / Ambient temperature View Scheme

1: 75 percent / 2 h / 140 °C 2: 1.) potassium tert-butoxide / 1.) THF-DMSO, 2.) r.t., occasional sonication, 50 min 3: 92 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature 4: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min View Scheme

1: 75 percent / 2 h / 140 °C 2: 1.) potassium tert-butoxide / 1.) THF-DMSO, 2.) r.t., occasional sonication, 50 min 3: 93 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature 4: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min 5: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 6: 86 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 7: 89 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature View Scheme

1: 75 percent / 2 h / 140 °C 2: 1.) potassium tert-butoxide / 1.) THF-DMSO, 2.) r.t., occasional sonication, 50 min 3: 85 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature 4: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min 5: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 6: 88 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 7: 88 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature 8: 96 percent / boron tribromide / CH2Cl2 / 0.33 h / Ambient temperature View Scheme

1: 75 percent / 2 h / 140 °C 2: 1.) potassium tert-butoxide / 1.) THF-DMSO, 2.) r.t., occasional sonication, 50 min 3: 83 percent / hydrogen / 10 percent Pd-C / ethanol / 24 h / 2942.03 Torr / Ambient temperature 4: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 15 min, 2.) -78 deg C, 5 min, then r.t., 20 min 5: 1.) lithium diisopropylamide, 2.) hexamethylphosphoric triamide / 1.) THF, -78 deg C, 2 h, 2.) -78 deg C, 1 h, then -15 deg C, 30 min 6: 91 percent / p-toluenesulfonic acid / benzene / 1 h / Heating 7: 88 percent / hydrogen / 10 percent Pd-C / acetone / 6 h / 2574.3 Torr / Ambient temperature 8: 97 percent / boron tribromide / CH2Cl2 / 0.17 h / Ambient temperature View Scheme