1: 1.) H2, KOAc, 2.) MnO2 / 1.) 10percent Pd/C / 1.) MeOH, 40 psi, 1.25 h, 2.) CH2Cl2, reflux 2: 1.) LDA / 1.) THF, hexane, -78 deg C, 60 min, 2.) THF, hexane, -78 deg C, 10 min 3: (dimethylamino)pyridine / CH2Cl2 / 19 h 4: DBU / toluene / 1 h / 100 °C 5: 70 percent / 10percent aq. NaOH / ethanol / 17 h / Ambient temperature View Scheme

hydrogen; potassium acetate; palladium on activated charcoal in methanol

in methanol; potassium acetate

1: 1.) H2, KOAc, 2.) MnO2 / 1.) 10percent Pd/C / 1.) MeOH, 40 psi, 1.25 h, 2.) CH2Cl2, reflux 2: 1.) LDA / 1.) THF, hexane, -78 deg C, 60 min, 2.) THF, hexane, -78 deg C, 10 min 3: (dimethylamino)pyridine / CH2Cl2 / 19 h 4: DBU / toluene / 1 h / 100 °C View Scheme