1: 80 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 °C 2: 80 percent / pyridinium p-toluenesulfonate / 3 h / Ambient temperature 3: BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 4: 64 percent / BF3*THF / tetrahydrofuran / 1.) room temp., 15 min, 2.) reflux, 24 h 5: 80 percent / 5percent aq. NaOH / 1 h / Ambient temperature 6: Et3N / CH2Cl2 / 1 h / Ambient temperature 7: DBU / toluene / 1 h / 100 °C 8: 1.) O3, 2.) Me2S / 1.) MeOH, -78 deg C, 2.) -78 deg C to room temp. 9: Jones reagent / acetone / 2 h / 0 °C View Scheme

1: 80 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 °C 2: 80 percent / pyridinium p-toluenesulfonate / 3 h / Ambient temperature 3: BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 4: 64 percent / BF3*THF / tetrahydrofuran / 1.) room temp., 15 min, 2.) reflux, 24 h 5: 80 percent / 5percent aq. NaOH / 1 h / Ambient temperature 6: Et3N / CH2Cl2 / 1 h / Ambient temperature 7: DBU / toluene / 1 h / 100 °C 8: 1.) O3, 2.) Me2S / 1.) MeOH, -78 deg C, 2.) -78 deg C to room temp. 9: Jones reagent / acetone / 2 h / 0 °C View Scheme

1: 80 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 °C 2: 80 percent / pyridinium p-toluenesulfonate / 3 h / Ambient temperature 3: BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 4: 64 percent / BF3*THF / tetrahydrofuran / 1.) room temp., 15 min, 2.) reflux, 24 h 5: 80 percent / 5percent aq. NaOH / 1 h / Ambient temperature 6: Et3N / CH2Cl2 / 1 h / Ambient temperature 7: DBU / toluene / 1 h / 100 °C 8: 1.) O3, 2.) Me2S / 1.) MeOH, -78 deg C, 2.) -78 deg C to room temp. View Scheme

1: 80 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 °C 2: 80 percent / pyridinium p-toluenesulfonate / 3 h / Ambient temperature 3: 70 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature 4: 1.) BH3*THF, 2.) 5percent aq. NaOH / 1.) THF, room temp., 15 min; reflux, 24 h, 2.) CH2Cl2, 0 deg C, 30 min; room temp., 30 min 5: 77 percent / PDC, 4 Angstroem molecular sieves / CH2Cl2 / 5 h / Ambient temperature 6: 60 percent / 5percent KOH / ethanol / 1 h / Heating 7: 87 percent / AIBN, Bu3SnH / benzene / 3 h / Heating 8: 55 percent / LiAlH4 / tetrahydrofuran / 1.) room temp., 1 h, 2.) reflux, 1 h View Scheme