1: 0.36 g / H2O, pyridinium p-toluenesulfonate / acetone / 2 h / Heating 2: 51 percent / Jones reagent / acetone / 1) -10 deg C, 15 min, 2.) 0 deg C, 15 min View Scheme

1: 1) lithium diisopropylamide / 1) THF-hexane, -75 deg C, 40 min, 2) THF-hexane, -75 deg C, 1h, then 20 deg C, 1 h View Scheme

1: 95 percent / lithium diisopropylamide / hexane; tetrahydrofuran / 1) -70 deg C, 1 h, 2) 20 deg C, 1 h 2: 85.5 percent / pyridinium p-toluenesulfonate / acetone; H2O / 2 h / Heating 3: 1) butyllithium / 1) THF-hexan, -78 deg C, 1.5 h, 2) -78 deg C, 1 h, room temperature, 15 h View Scheme

1: 95 percent / lithium diisopropylamide / hexane; tetrahydrofuran / 1) -70 deg C, 1 h, 2) 20 deg C, 1 h 2: 85.5 percent / pyridinium p-toluenesulfonate / acetone; H2O / 2 h / Heating 3: 1) butyllithium / 1) THF-hexan, -78 deg C, 1.5 h, 2) -78 deg C, 1 h, room temperature, 15 h 4: 66 percent / N-bromosuccinimide / tetrahydrofuran; H2O / 1) 0 deg C, 1.5h, 2) 20 deg C, 1 h View Scheme

1: 86 percent / pyridine, piperidine / 3 h / 120 °C 2: 70 percent / sodium borohydride / methanol / 1.) 5 deg C, 15 min, 2.) 20 deg C, 0.5 h 3: 2.33 g / TsOH*Py / acetone; H2O / 2 h / Heating 4: 1.) butyllithium / 1.) THF, hexane, -78 deg C, 1 h, 2.)a) THF, hexane, -78 deg C, 1 h, b) 20 deg C, 15 h 5: sodium hydroxide / H2O; methanol / 2 h / Heating 6: quinoline / Heating 7: thionyl chloride / dimethylformamide / 1 h / 30 °C 8: 1 h / 20 °C View Scheme