Multi-step reaction with 14 steps
1: 88 percent / DIBAL / toluene / 0.5 h / -78 °C
2: Et3N / CH2Cl2 / 0.5 h / -78 °C
3: LiBr / tetrahydrofuran; CH2Cl2 / 1 h / -20 °C
4: NaH, n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.) 0 deg C, 15 min; 0 deg C, 30 min, 2.) -20 deg C, 15 h
5: 31 percent / SnCl4 / CH2Cl2; H2O / 2 h / 0 °C
6: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h
7: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h
8: 94 percent / DIBAL / toluene / 1 h / -78 °C
9: 99 percent / pyridine, DMAP / 0.5 h / 0 °C
10: 1.) n-BuLi, Me3SnCl, 2.) LiCl / 2.) Pd(dba)2 / 1.) THF, hexane, -50 deg C, 0.5 h; -50 deg C, 3 h, 2.) DMF, 100 deg C, 4 h
11: 71 percent / CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.5 h / -20 °C
12: 43 percent / BBr3 / CH2Cl2 / 2.5 h / -78 - -10 °C
13: 62 percent / BF3*Et2O / CH2Cl2 / 1 h / Ambient temperature
14: 67 percent / Raney nickel W-7 / ethanol / 3 h / Heating
With
pyridine; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; dmap; copper(l) iodide; n-butyllithium; boron trifluoride diethyl etherate; trimethyltin(IV)chloride; boron tribromide; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; triethylamine; lithium chloride; lithium bromide;
Raney nickel W-7; bis(dibenzylideneacetone)-palladium(0);
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; water; toluene;