Multi-step reaction with 8 steps
1: 95 percent / imidazole / dimethylformamide / 5 h / Ambient temperature
2: 1.) 4 percent O3 in O2, 2.) Me2S / 1.) CH2Cl2, MeOH, -78 deg C., 1 h, 2.) CH2Cl2, MeOH, from - 78 to RT, 12 h
3: 92 percent / p-toluenesulfonic acid / benzene / 18 h / Heating
4: 95 percent / LDA / hexane; tetrahydrofuran / 1.) -78 deg C., 2 h, 2.) from -78 to RT, 15 h
5: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C
6: 97 percent / DMAP, Et3N / CH2Cl2 / 2.5 h / 0 °C
7: 89 percent / lithium triethylborohydride / tetrahydrofuran / 18 h / Ambient temperature
8: 86 percent / Pd(II)Cl2, Cu(I)Cl, O2 / dimethylformamide; H2O / 18 h
With
1H-imidazole; dmap; copper(l) iodide; lithium aluminium tetrahydride; dimethylsulfide; oxygen; lithium triethylborohydride; toluene-4-sulfonic acid; ozone; triethylamine; palladium dichloride; lithium diisopropyl amide;
In
tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/0040-4020(96)00284-0