Multi-step reaction with 7 steps
1: 1.) sodium hexamethyldisilazide / 1.) THF, room temperature, 10 min, 2.) THF
2: 1.) n-butyllithium / 1.) ether, pentane, 5 min, 2.) ether, pentane, 20 min
3: 1.) 18-crown-6, potassium hexamethyldisilazide / 1.) THF, toluene, -78 -> -30 deg C, 2.) THF, toluene, 2 h
4: 41 percent / pyridine, osmium tetraoxide / 2 h
5: 73 percent / imidazole, 4-(N,N-dimethylamino)pyridine / dimethylformamide / Ambient temperature
6: 1.) thexylborane, 2.) KOH, H2O2 / 1.) THF, 0 deg C, 30 min, 2.) water, THF, 12 h
7: 82 percent / Dess-Martin periodinane / CH2Cl2 / 1 h
With
pyridine; 1H-imidazole; dmap; potassium hydroxide; osmium(VIII) oxide; n-butyllithium; 18-crown-6 ether; thexylborane; dihydrogen peroxide; sodium hexamethyldisilazane; potassium hexamethylsilazane; Dess-Martin periodane;
In
dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo981749j