base in acetone

1: 90 percent / KF, 18-crown-6 2: 2.)H2SO4 / 1. and 2. MeOH 3: 60 percent / aq. HCl / acetone / Heating 4: 1.) DBN 2.) pyrrolidine, HOAc 5: 59 percent / BF3*Et2O / CH2Cl2 / 0 °C 6: diisobutylaluminum hydride (DIBAL) / toluene / -78 °C 7: 53 percent / sodium cyanoborohydride (NaCNBH3) / 2-methyl-propan-2-ol 8: N-chlorosuccinimide, AgNO3 / acetonitrile View Scheme

1: KOH 2: 90 percent / KF, 18-crown-6 3: 2.)H2SO4 / 1. and 2. MeOH 4: 60 percent / aq. HCl / acetone / Heating 5: 1.) DBN 2.) pyrrolidine, HOAc 6: 59 percent / BF3*Et2O / CH2Cl2 / 0 °C 7: diisobutylaluminum hydride (DIBAL) / toluene / -78 °C 8: 53 percent / sodium cyanoborohydride (NaCNBH3) / 2-methyl-propan-2-ol 9: N-chlorosuccinimide, AgNO3 / acetonitrile View Scheme

1: 1.) DBN 2.) pyrrolidine, HOAc 2: 59 percent / BF3*Et2O / CH2Cl2 / 0 °C 3: diisobutylaluminum hydride (DIBAL) / toluene / -78 °C 4: 53 percent / sodium cyanoborohydride (NaCNBH3) / 2-methyl-propan-2-ol 5: N-chlorosuccinimide, AgNO3 / acetonitrile View Scheme

1: 2.)H2SO4 / 1. and 2. MeOH 2: 60 percent / aq. HCl / acetone / Heating 3: 1.) DBN 2.) pyrrolidine, HOAc 4: 59 percent / BF3*Et2O / CH2Cl2 / 0 °C 5: diisobutylaluminum hydride (DIBAL) / toluene / -78 °C 6: 53 percent / sodium cyanoborohydride (NaCNBH3) / 2-methyl-propan-2-ol 7: N-chlorosuccinimide, AgNO3 / acetonitrile View Scheme

potassium hydroxide in ethanol 0.583333 h; Heating;

1: 1.) Mg / 1.) THF, reflux, 2.) reflux, 4 h 2: p-toluenesulfonic acid / benzene / 0.5 h / Heating 3: p-toluenesulfonic acid / methanol / 24 h / Ambient temperature 4: Zn / diethyl ether / 0.5 h / Heating 5: Zn, NH4Cl / methanol / 3 h / Heating 6: molecular sieves 3A, pyridine / 72 h / Ambient temperature 7: 1.) p-toluenesulfonyl chloride, 2.) H2O / 1.) pyridine, 0 deg C, 15 h, 2.) overnight 8: 94 percent / K2CO3 / methanol / 3 h / Ambient temperature 9: 90 percent / BH3*THF / tetrahydrofuran / 2 h / Heating 10: 91 percent / Jones reagent / acetone / 0.33 h / 0 °C 11: 71 percent / base / acetone View Scheme

1: Zn / diethyl ether / 0.5 h / Heating 2: Zn, NH4Cl / methanol / 3 h / Heating 3: molecular sieves 3A, pyridine / 72 h / Ambient temperature 4: 1.) p-toluenesulfonyl chloride, 2.) H2O / 1.) pyridine, 0 deg C, 15 h, 2.) overnight 5: 94 percent / K2CO3 / methanol / 3 h / Ambient temperature 6: 90 percent / BH3*THF / tetrahydrofuran / 2 h / Heating 7: 91 percent / Jones reagent / acetone / 0.33 h / 0 °C 8: 71 percent / base / acetone View Scheme

1: p-toluenesulfonic acid / 0.67 h / Ambient temperature 2: 1.) Mg / 1.) THF, reflux, 2.) reflux, 4 h 3: p-toluenesulfonic acid / benzene / 0.5 h / Heating 4: p-toluenesulfonic acid / methanol / 24 h / Ambient temperature 5: Zn / diethyl ether / 0.5 h / Heating 6: Zn, NH4Cl / methanol / 3 h / Heating 7: molecular sieves 3A, pyridine / 72 h / Ambient temperature 8: 1.) p-toluenesulfonyl chloride, 2.) H2O / 1.) pyridine, 0 deg C, 15 h, 2.) overnight 9: 94 percent / K2CO3 / methanol / 3 h / Ambient temperature 10: 90 percent / BH3*THF / tetrahydrofuran / 2 h / Heating 11: 91 percent / Jones reagent / acetone / 0.33 h / 0 °C 12: 71 percent / base / acetone View Scheme

1: 67 percent / sodium amide / benzene / 2.5 h / Heating 2: 80 percent / sodium amide / benzene / 5 h / Heating 3: 1.) diisobutylaluminium hydride, 2.) 10percent (v/v) methanolic hydrochloric acid / 1.) benzene, 2.) heating View Scheme