Multi-step reaction with 11 steps
1: ethyl acetate
2: 93 percent / DMAP / CH2Cl2 / Ambient temperature
3: 86 percent / dimethylsulfoxide / 2 h / 65 °C
4: 90 percent / diisobutylaluminum hydride / toluene; CH2Cl2 / 0.42 h / 0 °C
5: 1.) Zn / 1.) THF, reflux, 10 min, 2.) THF, reflux, 10 min
6: 67 percent / diethyl ether / a) 0 deg C, 30 min, b) RT, 2 h
7: DMAP / CH2Cl2 / 0.5 h / Ambient temperature
8: Bu3SnH, 2,2'-azobisisobutyronitrile / toluene / 0.5 h / Heating
9: camphorsulfonic acid / methanol; CHCl3 / Ambient temperature
10: 98 percent / K2CO3 / dimethylsulfoxide / 48 h / 110 - 115 °C
11: 1.) ether, 0 deg C, irradiation, 6 min, 2.) C2H5OH, reflux, 1 h
With
dmap; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; tri-n-butyl-tin hydride; diisobutylaluminium hydride; potassium carbonate; zinc;
In
methanol; diethyl ether; dichloromethane; chloroform; dimethyl sulfoxide; ethyl acetate; toluene;
DOI:10.1248/cpb.44.62