Multi-step reaction with 11 steps
1: pyridinium p-toluenesulfonate / CH2Cl2 / 7 h / Ambient temperature
2: lithium aluminum hydride / diethyl ether / 0.5 h / Ambient temperature
3: 1.) n-butyllithium / 1.) tetrahydrofuran, room temperature, 20 min, 2.) -78 deg C --> room temperature
4: 1.) iodine, sodium bicarbonate, 2.) conc. hydrochloric acid / 1.) acetonitrile, 0 deg C, 10 min, 2.) tetrahydrofuran, 20 min, room temperature
5: 80 percent / amalgamated zinc / ethanol / 1 h / Heating
6: pyridine / toluene; CH2Cl2 / 1.) 0 deg C --> room temperature, 2.) 10 min, rt
7: 1.) ozone, 2.) dimethylsulfide / 1.) methanol, dichloromethane, -78 deg C, 10 min, 2.) 0 deg C, 1 h
8: sodium borohydride / ethanol / 0.17 h / 0 °C
9: 80 percent / triphenylphosphine, iodine, imidazole / benzene / 0.5 h / Ambient temperature
10: 92 percent / amalgamated zinc, ammoniumchloride / ethanol / 20 h / Heating
11: 1.) methyllithium, 2.) dicamphorsulfonic acid / 1.) ether, -78 deg C --> -20 deg C, 2.) dichloromethane, room temperature, 20 min
With
pyridine; 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; amalgamated zinc; dimethylsulfide; dicamphorsulfonic acid; ammonium chloride; methyllithium; iodine; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; ozone; triphenylphosphine;
In
diethyl ether; ethanol; dichloromethane; toluene; benzene;
DOI:10.1016/S0040-4020(01)97592-1