Multi-step reaction with 17 steps
1: 22 percent / DDQ / CH2Cl2; H2O / 0.5 h / Ambient temperature
2: 1) NaH, 2) t-BuOK / 1) THF, room temperature, 2 h, 2) MeOH, room temperature, 18 h
3: 75 percent / TfOH / diethyl ether / 0.17 h / Ambient temperature
4: 100 percent / LiAlH4 / diethyl ether / 0.5 h / -5 °C
5: 95 percent / NEt3, DMAP / CH2Cl2 / 9 h / Ambient temperature
6: 100 percent / DDQ / CH2Cl2; H2O / 0.67 h / Ambient temperature
7: 44 percent / H2 / Pd(OH)2-C / ethanol; ethyl acetate / 168 h / 760 Torr / Ambient temperature
8: 96 percent / p-TsOH*H2O / 0.5 h / Ambient temperature
9: 99 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 31 h / Ambient temperature
10: 94 percent / p-TsOH*H2O / methanol / 0.83 h / Ambient temperature
11: 83 percent / NEt3, DMAP / CH2Cl2 / 3 h / Ambient temperature
12: 86 percent / NaI / acetone / 8 h / 50 °C
13: 98 percent / NEt3 / CH2Cl2 / 0.17 h / -10 °C
14: 98 percent / acetonitrile / 27 h / 60 °C
15: 1) NaHMDS / 1) THF, room temperature, 1 h, 2) THF, room temperature, 30 min
16: 96 percent / K2CO3 / methanol / 1.5 h / 0 °C
17: 38 percent / tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)europium / toluene / 21 h / 80 °C
With
dmap; lithium aluminium tetrahydride; tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); trifluorormethanesulfonic acid; potassium tert-butylate; hydrogen; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide;
palladium hydroxide - carbon;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile;
DOI:10.1016/S0040-4020(97)10254-X