1: diethyl ether / 1) RT, 20 min, 2) reflux, 30 min 2: 1.31 g / 4 N HCl / benzene; H2O / 0.17 h 3: 57.2 percent / 10percent Pd/C / decahydronaphthalene / 15 h / Heating 4: 85 percent / BBr3 / CH2Cl2 / 2.5 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 View Scheme

in diethyl ether

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: 1) 70percent HClO4, 2) DDQ / 1) CCl4, RT, 3 h, 2) benzene, RT, 3.5 h 6: 232 mg / NaOMe / methanol / 0.25 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: diethyl ether / 1) RT, 20 min, 2) reflux, 30 min 2: 1.31 g / 4 N HCl / benzene; H2O / 0.17 h 3: 57.2 percent / 10percent Pd/C / decahydronaphthalene / 15 h / Heating View Scheme