Multi-step reaction with 14 steps
1: 40 percent / sodium hydride / tetrahydrofuran; dimethylformamide / 1.) 0 deg C, 1 h, 2.) room temperature, 12 h
2: 68 percent / Jones reagent
3: 98 percent
4: 46 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C
5: 74 percent / 30percent H2O2, sodium hydrocarbonate / tetrahydrofuran / 1.) 0 deg C, 2.) room temperature, 1 h
6: 93 percent / diisobutylaluminum hydride / CH2Cl2; toluene / 0.5 h / -78 °C
7: 74 percent / tetra-iso-propyl titanate, L-(+)-diethyl tartrate, molecular sieves 3A / CH2Cl2 / 3 h / -25 °C
8: 40 percent / sodium bis(2-methoxyethoxy)aluminum hydride, (+)-diisopropyl tartrate / tetrahydrofuran; toluene / 1.) 0 deg C, 2 h, 2.) room temperature, 72 h
9: 59 percent / sodium hydride / dimethylformamide / 1 h / 0 °C
10: 61 percent / lithium aluminum hydride / tetrahydrofuran / 4 h / 0 °C
11: 51 percent / imidazole / dimethylformamide / 24 h / Ambient temperature
12: 79 percent / hydrogen / 10percent palladium carbon
13: 69 percent / pyridinium dichromate, molecular sieves 3A / CH2Cl2
14: 1.) 30percent H2O2, sodium dihydrogenphosphate, sodium chloride / 1.) H2O, acetonitrile, 0 deg C, 2 h
With
1H-imidazole; titanium(IV) isopropylate; sodium dihydrogenphosphate; lithium aluminium tetrahydride; dipyridinium dichromate; jones reagent; L-(+)-diisopropyl tartrate; diethyl (2R,3R)-tartrate; 3 A molecular sieve; hydrogen; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium chloride; lithium diisopropyl amide;
palladium carbon;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;