Multi-step reaction with 6 steps
1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 deg C, 1 h
2: 78 percent / TFAA, DMSO / CH2Cl2 / 0.5 h / -55 °C
3: 1.) s-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) 0 deg C, 1 h, b) RT, 3 h
4: 2.) 1-octene / 2.) 10percent Pd/C / 1.) toluene, reflux, 20 h, 2.) toluene, reflux, 48 h
5: 75 percent / H2O, DDQ / CH2Cl2 / 4 h / Ambient temperature
6: 53 percent / pyridine / 2.5 h / 0 - 20 °C
With
pyridine; n-butyllithium; oct-1-ene; water; sec.-butyllithium; dimethyl sulfoxide; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium on activated charcoal;
In
dichloromethane;
DOI:10.1021/jm950881y