Multi-step reaction with 12 steps
1: 82 percent / zinc triflate / CH2Cl2 / 2 h / Ambient temperature
2: 89 percent / methanolic t-BuOK / methyl acetate / 2 h / Ambient temperature
3: 80 percent / p-toluenesulfonic acid / CH2Cl2 / 1 h / Ambient temperature
4: 94 percent / DIBAL / tetrahydrofuran / 0.5 h / -78 °C
5: 1.) lithium bis(trimethylsilyl)amide, HMPA / 1.) THF, 0 deg C, 30 min, 2.) THF, -40 -> 0 deg C, 30 min
7: 80 percent / CH2Cl2 / 0.5 h / 0 °C
8: 88 percent / cation exchange resin AG50-X8 / methanol / 6 h / 23 °C
9: triethylamine / CH2Cl2 / 0.5 h / -20 °C
10: 18-crown-6-ether / toluene / 8 h / 115 °C
11: 71 percent / aq. ceric ammonium nitrate / acetonitrile / 1 h / Ambient temperature
12: aq. LiOH / 1,2-dimethoxy-ethane / 1 h / 60 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; ammonium cerium(IV) nitrate; 18-crown-6 ether; cation exchange resin AG50-X8; potassium tert-butylate; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; acetic acid methyl ester; toluene; acetonitrile;