2-cyclohexene-1,4-dione; pyridinium p-toluenesulfonate in toluene 8 h; Heating;

1.1: N,N-diethylaniline / 4 h / Heating 2.1: triethylamine / CH2Cl2 / 0 - 20 °C 3.1: OsO4; NaIO4 / diethyl ether; acetone; H2O / 8 h 3.2: sodium borohydride / methanol / 0.5 h / 0 °C 4.1: tetra-n-butylammonium fluoride / CH2Cl2; tetrahydrofuran / 1 h / 0 - 20 °C 5.1: 98 percent / ceric ammonium nitrate / acetonitrile; H2O / 0.08 h 6.1: 75 percent / pyridinium p-toluenesulfonate; dihydro-1,4-benzoquinone / toluene / 8 h / Heating View Scheme

1.1: N,N-diethylaniline / 4 h / Heating 2.1: triethylamine / CH2Cl2 / 0 - 20 °C 3.1: OsO4; NaIO4 / diethyl ether; acetone; H2O / 8 h 3.2: sodium borohydride / methanol / 0.5 h / 0 °C 4.1: tetra-n-butylammonium fluoride / CH2Cl2; tetrahydrofuran / 1 h / 0 - 20 °C 5.1: 98 percent / ceric ammonium nitrate / acetonitrile; H2O / 0.08 h 6.1: 75 percent / pyridinium p-toluenesulfonate; dihydro-1,4-benzoquinone / toluene / 8 h / Heating View Scheme

1: 98 percent / ceric ammonium nitrate / acetonitrile; H2O / 0.08 h 2: 75 percent / pyridinium p-toluenesulfonate; dihydro-1,4-benzoquinone / toluene / 8 h / Heating View Scheme

1.1: triethylamine / CH2Cl2 / 0 - 20 °C 2.1: OsO4; NaIO4 / diethyl ether; acetone; H2O / 8 h 2.2: sodium borohydride / methanol / 0.5 h / 0 °C 3.1: tetra-n-butylammonium fluoride / CH2Cl2; tetrahydrofuran / 1 h / 0 - 20 °C 4.1: 98 percent / ceric ammonium nitrate / acetonitrile; H2O / 0.08 h 5.1: 75 percent / pyridinium p-toluenesulfonate; dihydro-1,4-benzoquinone / toluene / 8 h / Heating View Scheme

potassium carbonate; acetone

1: acetic acid; aqueous HBr 2: potassium carbonate; acetone View Scheme