Multi-step reaction with 13 steps
1: 73 percent / potassium hydroxide / H2O / 2 h
2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 -> -30 deg C, 2 h
3: 95 percent / 2,6-lutidine / CH2Cl2 / 2 h / Ambient temperature
4: 1.) n-BuLi / 1.) toluene, ether, hexane, -78 -> 0 deg C, 2.) toluene, ether, hexane, -78 -> -10 deg C
5: 95 percent / HCl / methanol
6: 97 percent / NaBH4 / dioxane; methanol / 1 h
7: 1.) NaH / 1.) DMF, mineral oil, room temperature, 30 min, 2.) DMF, mineral oil, 0 deg C, 5 h
8: 80 percent / sodium nitrite, acetic acid / dimethylsulfoxide / 8 h / 37 °C
9: 71 percent / triethylamine, diphenylphosphoryl azide / 48 h / Heating
10: 1.) ozone, 2.) dimethyl sulfide / 1.) ethanol, -78 deg C, 2.) ethanol, room temperature, overnight
11: 50 mg / NaBH4 / methanol / 1 h
12: triethylamine / CH2Cl2 / 1 h / 0 °C
13: 32 mg / NaH / tetrahydrofuran; paraffin / 10 h / Ambient temperature
With
2,6-dimethylpyridine; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; dimethylsulfide; diphenylphosphoranyl azide; sodium hydride; ozone; acetic acid; triethylamine; sodium nitrite;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; paraffin;
DOI:10.1021/jo981577q