Multi-step reaction with 12 steps
1: 1.) NaH / 1.) DMF, 0 deg C, 1.5 h 2.) DMF, room temperature, overnight
2: 1.) LDA / 1.) hexanes, THF, -78 deg C, 30 min 2.) hexanes, THF, -78 deg c - 1 h, room temperature - overnight
3: 90 percent / K, t-BuOH / diethyl ether; hexamethylphosphoric acid triamide / 12 h / 0 - 20 °C
4: 99 percent / pyridinium dichromate, pyridinium tosylate / CH2Cl2 / 12 h / 0 °C
5: 1.) LDA / 1.) hexanes, THF, -78 deg C - 1 h, room temperature - 1 h, 2.) hexanes, THF, -78 deg C - room temperature, overnight
6: 0.922 g / palladium (2) acetate / acetonitrile / 20 h
8: 1.) MeLi / 1.) Et2O, THF, room temperature, 25 min, 2.) Et2O, THF, -78 deg C - room temperature, overnight
9: 78 percent / Et3N, bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 75 °C
10: 80 percent / H2, Lindlar catalyst, quinoline / hexane
11: 100 percent / 2,2,4-trimethyl-pentane / 5 h / Heating
12: 81 percent / AG 50W-X4 resin / 32 h / Ambient temperature
With
quinoline; bis-triphenylphosphine-palladium(II) chloride; palladium diacetate; Lindlar's catalyst; dipyridinium dichromate; AG 50W-X4 resin; methyllithium; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; tert-butyl alcohol; lithium diisopropyl amide;
In
N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(97)00692-3