1: 97.3 percent / polyphosphoric acid / 87 °C / 1) 1 min, 2) 30 min 2: diethyl ether / 1) RT, 20 min, 2) reflux, 30 min 3: 1.31 g / 4 N HCl / benzene; H2O / 0.17 h 4: 94 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O / 48 h / 23 °C 5: 97 percent / p-TsOH monohydrate / benzene 6: hexamethyldisilazane / CH2Cl2 / 1.) -10 deg C, 1 h, 2.) room temperature 7: 80 mg / N-methylmorpholine N-oxide hydrate, OsO4 / Triton B / 2-methyl-propan-2-ol; H2O / 1.67 h / 10 °C 8: 482 mg / dichlorodicyanobenzoquinone / benzene / 24 h / Ambient temperature 9: 37.6 percent / EtSH, AlCl3 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 94 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O / 48 h / 23 °C 2: 97 percent / p-TsOH monohydrate / benzene 3: hexamethyldisilazane / CH2Cl2 / 1.) -10 deg C, 1 h, 2.) room temperature 4: 80 mg / N-methylmorpholine N-oxide hydrate, OsO4 / Triton B / 2-methyl-propan-2-ol; H2O / 1.67 h / 10 °C 5: 482 mg / dichlorodicyanobenzoquinone / benzene / 24 h / Ambient temperature 6: 37.6 percent / EtSH, AlCl3 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 97 percent / p-TsOH monohydrate / benzene 2: hexamethyldisilazane / CH2Cl2 / 1.) -10 deg C, 1 h, 2.) room temperature 3: 80 mg / N-methylmorpholine N-oxide hydrate, OsO4 / Triton B / 2-methyl-propan-2-ol; H2O / 1.67 h / 10 °C 4: 482 mg / dichlorodicyanobenzoquinone / benzene / 24 h / Ambient temperature 5: 37.6 percent / EtSH, AlCl3 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: diethyl ether / 1) RT, 20 min, 2) reflux, 30 min 2: 1.31 g / 4 N HCl / benzene; H2O / 0.17 h 3: 94 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O / 48 h / 23 °C 4: 97 percent / p-TsOH monohydrate / benzene 5: hexamethyldisilazane / CH2Cl2 / 1.) -10 deg C, 1 h, 2.) room temperature 6: 80 mg / N-methylmorpholine N-oxide hydrate, OsO4 / Triton B / 2-methyl-propan-2-ol; H2O / 1.67 h / 10 °C 7: 482 mg / dichlorodicyanobenzoquinone / benzene / 24 h / Ambient temperature 8: 37.6 percent / EtSH, AlCl3 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 24.4 percent / diethyl ether / 1 h / Heating 2: 93 percent / zinc amalgame, aq. HCl / toluene / 62 h / Heating 3: 97.3 percent / polyphosphoric acid / 87 °C / 1) 1 min, 2) 30 min 4: diethyl ether / 1) RT, 20 min, 2) reflux, 30 min 5: 1.31 g / 4 N HCl / benzene; H2O / 0.17 h 6: 94 percent / N-methylmorpholine N-oxide hydrate, OsO4 / acetone; H2O / 48 h / 23 °C 7: 97 percent / p-TsOH monohydrate / benzene 8: hexamethyldisilazane / CH2Cl2 / 1.) -10 deg C, 1 h, 2.) room temperature 9: 80 mg / N-methylmorpholine N-oxide hydrate, OsO4 / Triton B / 2-methyl-propan-2-ol; H2O / 1.67 h / 10 °C 10: 482 mg / dichlorodicyanobenzoquinone / benzene / 24 h / Ambient temperature 11: 37.6 percent / EtSH, AlCl3 / CH2Cl2 / 2 h / Ambient temperature View Scheme

aluminium trichloride; ethanethiol in dichloromethane 2 h; Ambient temperature;

1: hexamethyldisilazane / CH2Cl2 / 1.) -10 deg C, 1 h, 2.) room temperature 2: 80 mg / N-methylmorpholine N-oxide hydrate, OsO4 / Triton B / 2-methyl-propan-2-ol; H2O / 1.67 h / 10 °C 3: 482 mg / dichlorodicyanobenzoquinone / benzene / 24 h / Ambient temperature 4: 37.6 percent / EtSH, AlCl3 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 80 mg / N-methylmorpholine N-oxide hydrate, OsO4 / Triton B / 2-methyl-propan-2-ol; H2O / 1.67 h / 10 °C 2: 482 mg / dichlorodicyanobenzoquinone / benzene / 24 h / Ambient temperature 3: 37.6 percent / EtSH, AlCl3 / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 482 mg / dichlorodicyanobenzoquinone / benzene / 24 h / Ambient temperature 2: 37.6 percent / EtSH, AlCl3 / CH2Cl2 / 2 h / Ambient temperature View Scheme