Multi-step reaction with 12 steps
1: 4-dimethylaminopyridine / diethyl ether / 1.5 h / Ambient temperature
2: tributyltin hydride / toluene / 16 h / Heating
3: 0.02 M methanolic sodium methoxide / 2 h / Ambient temperature
4: 1.) p-toluenesulfonyl chloride, pyridine, 2.) 1.17 N aq. KOH / 1.) CHCl3, -50 deg C, 3 h; room temperature, 20 h, 2.) MeOH
5: n-BuLi / hexamethylphosphoric acid triamide / 20 h / Ambient temperature
6: diethyl ether
7: hydrogen, ethylene diamine / nickel acetate/sodium borohydride / ethanol
8: imidazole / dimethylformamide / 17 h / 78 °C
9: zinc chloride / 1 h / -10 °C
10: p-toluenesulfonic acid / acetone / 1 h / Ambient temperature
11: mercuric oxide, mercuric chloride / acetone; H2O / 8 h / Ambient temperature
12: 90 percent / dimethylformamide / 20 h / Ambient temperature
With
pyridine; 1H-imidazole; dmap; potassium hydroxide; n-butyllithium; hydrogen; tri-n-butyl-tin hydride; sodium methylate; toluene-4-sulfonic acid; ethylenediamine; p-toluenesulfonyl chloride; mercury dichloride; mercury(II) oxide; zinc(II) chloride;
sodium tetrahydroborate; nickel diacetate;
In
N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; water; N,N-dimethyl-formamide; acetone; toluene;