Multi-step reaction with 9 steps
1: 63 percent / DBU / ethanol / 40 h / Ambient temperature
2: 96 percent / MnO2 / CH2Cl2
3: 98 percent / DIBAL, CuI / toluene; hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C
4: 93 percent / NaBH4, CeCl3*7H2O / methanol
5: 98 percent / imidazole / dimethylformamide
6: 85 percent / LiBH4 / tetrahydrofuran
7: 88 percent / NaHCO3 / diphenyl ether / 0.5 h / 260 °C
8: 94 percent / DMAP, pyridine
9: 93 percent / Bu4NF / tetrahydrofuran
With
pyridine; 1H-imidazole; dmap; manganese(IV) oxide; sodium tetrahydroborate; copper(l) iodide; lithium borohydride; cerium(III) chloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diphenylether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1055/s-1998-1851