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: 57.2 percent / 10percent Pd/C / decahydronaphthalene / 15 h / Heating 5: 85 percent / BBr3 / CH2Cl2 / 2.5 h / Ambient temperature View Scheme

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 View Scheme

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: 1) 70percent HClO4, 2) DDQ / 1) CCl4, RT, 3 h, 2) benzene, RT, 3.5 h 7: 232 mg / NaOMe / methanol / 0.25 h / Ambient temperature View Scheme

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: 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: 57.2 percent / 10percent Pd/C / decahydronaphthalene / 15 h / Heating View Scheme