Multi-step reaction with 9 steps
1: 91 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating
2: 99 percent / imidazole, pyridine / 0.5 h / 20 °C
3: 99 percent / CuI, NaI, K2CO3 / dimethylformamide / 20 h / 20 °C
4: 30 percent / LiAlH4 / diethyl ether / 3 h / Heating
5: ButOOH, Ti(OPri)4, 4 A molecular sieves, diethyl L-(+)-tartrate / CH2Cl2 / 72 h / -20 °C
6: 55 percent / Bu4NF / tetrahydrofuran / 1 h / 20 °C
7: 94 percent / imidazole / dimethylformamide / 1 h / 60 °C
8: 50 percent / Bu4NF / tetrahydrofuran; benzene / 4 h / 20 °C
9: 87 percent / pyridinium dichromate, 3 A molecular sieves, AcOH / CH2Cl2 / 2 h / 20 °C
With
pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; lithium aluminium tetrahydride; dipyridinium dichromate; diethyl (2R,3R)-tartrate; 3 A molecular sieve; 4 A molecular sieve; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; sodium iodide;
In
tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;