sodium hydride in dichloromethane 0.5 h; Ambient temperature;

1: 99 percent / CH2Cl2 2: 92 percent / Zn / benzene / Heating 3: 83 percent / Dess-Martin periodinane / CH2Cl2 4: 96 percent / toluene / Heating 5: 99 percent / HF / acetonitrile 6: NaH / CH2Cl2 View Scheme

1: 92 percent / Zn / benzene / Heating 2: 83 percent / Dess-Martin periodinane / CH2Cl2 3: 96 percent / toluene / Heating 4: 99 percent / HF / acetonitrile 5: NaH / CH2Cl2 View Scheme

1: 96 percent / toluene / Heating 2: 99 percent / HF / acetonitrile 3: NaH / CH2Cl2 View Scheme

2: 1.) lithium diisopropyl amide / tetrahydrofuran / -78 °C 3: toluene / 10 h / Heating 4: 48percent aq. HF / 1.5 h / 0 °C 5: diethyl ether / 0 °C 6: LiAlH4 / diethyl ether / 3 h 7: 91 percent / pyridine / CH2Cl2 / 0.5 h 8: 91 percent / pyridine / 9 h / Ambient temperature 9: 89 percent / Li, NH3 / tetrahydrofuran / 0.5 h / -78 °C / 1.) -78 deg C, 30 min. 2.) THF, 30 min 10: 100 percent / 48percent aq. HF / acetonitrile / 1 h 11: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min., 2.) CH2Cl2, -78 deg C to room temp. 12: 51 percent / BF3 * Et2O / CH2Cl2; diethyl ether / 2 h 13: 64 percent / toluene / 10 h / Heating 14: 79 percent / 48percent aq. HF / acetonitrile / 0.25 h 15: 100 percent / NaH / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

3: 1.) lithium diisopropyl amide / tetrahydrofuran / -78 °C 4: toluene / 10 h / Heating 5: 48percent aq. HF / 1.5 h / 0 °C 6: diethyl ether / 0 °C 7: LiAlH4 / diethyl ether / 3 h 8: 91 percent / pyridine / CH2Cl2 / 0.5 h 9: 91 percent / pyridine / 9 h / Ambient temperature 10: 89 percent / Li, NH3 / tetrahydrofuran / 0.5 h / -78 °C / 1.) -78 deg C, 30 min. 2.) THF, 30 min 11: 100 percent / 48percent aq. HF / acetonitrile / 1 h 12: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min., 2.) CH2Cl2, -78 deg C to room temp. 13: 51 percent / BF3 * Et2O / CH2Cl2; diethyl ether / 2 h 14: 64 percent / toluene / 10 h / Heating 15: 79 percent / 48percent aq. HF / acetonitrile / 0.25 h 16: 100 percent / NaH / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

2: 1.) lithium diisopropyl amide / tetrahydrofuran / -78 °C 3: toluene / 10 h / Heating 4: 48percent aq. HF / 1.5 h / 0 °C 5: diethyl ether / 0 °C 6: LiAlH4 / diethyl ether / 3 h 7: 91 percent / pyridine / CH2Cl2 / 0.5 h 8: 91 percent / pyridine / 9 h / Ambient temperature 9: 89 percent / Li, NH3 / tetrahydrofuran / 0.5 h / -78 °C / 1.) -78 deg C, 30 min. 2.) THF, 30 min 10: 100 percent / 48percent aq. HF / acetonitrile / 1 h 11: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min., 2.) CH2Cl2, -78 deg C to room temp. 12: 51 percent / BF3 * Et2O / CH2Cl2; diethyl ether / 2 h 13: 64 percent / toluene / 10 h / Heating 14: 79 percent / 48percent aq. HF / acetonitrile / 0.25 h 15: 100 percent / NaH / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

1: 91 percent / pyridine / CH2Cl2 / 0.5 h 2: 91 percent / pyridine / 9 h / Ambient temperature 3: 89 percent / Li, NH3 / tetrahydrofuran / 0.5 h / -78 °C / 1.) -78 deg C, 30 min. 2.) THF, 30 min 4: 100 percent / 48percent aq. HF / acetonitrile / 1 h 5: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min., 2.) CH2Cl2, -78 deg C to room temp. 6: 51 percent / BF3 * Et2O / CH2Cl2; diethyl ether / 2 h 7: 64 percent / toluene / 10 h / Heating 8: 79 percent / 48percent aq. HF / acetonitrile / 0.25 h 9: 100 percent / NaH / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

1: 1.) lithium diisopropyl amide / tetrahydrofuran / -78 °C 2: toluene / 10 h / Heating 3: 48percent aq. HF / 1.5 h / 0 °C 4: diethyl ether / 0 °C 5: LiAlH4 / diethyl ether / 3 h 6: 91 percent / pyridine / CH2Cl2 / 0.5 h 7: 91 percent / pyridine / 9 h / Ambient temperature 8: 89 percent / Li, NH3 / tetrahydrofuran / 0.5 h / -78 °C / 1.) -78 deg C, 30 min. 2.) THF, 30 min 9: 100 percent / 48percent aq. HF / acetonitrile / 1 h 10: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min., 2.) CH2Cl2, -78 deg C to room temp. 11: 51 percent / BF3 * Et2O / CH2Cl2; diethyl ether / 2 h 12: 64 percent / toluene / 10 h / Heating 13: 79 percent / 48percent aq. HF / acetonitrile / 0.25 h 14: 100 percent / NaH / CH2Cl2 / 0.5 h / Ambient temperature View Scheme

1: diethyl ether / 0 °C 2: LiAlH4 / diethyl ether / 3 h 3: 91 percent / pyridine / CH2Cl2 / 0.5 h 4: 91 percent / pyridine / 9 h / Ambient temperature 5: 89 percent / Li, NH3 / tetrahydrofuran / 0.5 h / -78 °C / 1.) -78 deg C, 30 min. 2.) THF, 30 min 6: 100 percent / 48percent aq. HF / acetonitrile / 1 h 7: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min., 2.) CH2Cl2, -78 deg C to room temp. 8: 51 percent / BF3 * Et2O / CH2Cl2; diethyl ether / 2 h 9: 64 percent / toluene / 10 h / Heating 10: 79 percent / 48percent aq. HF / acetonitrile / 0.25 h 11: 100 percent / NaH / CH2Cl2 / 0.5 h / Ambient temperature View Scheme