Multi-step reaction with 10 steps
1: 98 percent / PCC, Celite / CH2Cl2 / 3 h / Ambient temperature
3: 1.76 g / NaBH4 / methanol / 0.5 h / Ambient temperature
4: MnO2 / CH2Cl2 / 4 h
5: 78 percent / imidazole, DMF / CH2Cl2 / Ambient temperature
6: 63 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h
7: 75 percent / DIBAL / CH2Cl2 / 1 h / -78 °C
8: 86 percent / n-BuLi / 1.) THF, hexane, DMPU, 0 deg C, 20 min, 2.) THF, -78 deg C, 60 min
9: TBAF / tetrahydrofuran / 12 h / Ambient temperature
10: PCC, Celite / CH2Cl2 / 3 h / Ambient temperature
With
1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; Celite; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; N,N-dimethyl-formamide; pyridinium chlorochromate;
In
tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/jo971409i