Multi-step reaction with 6 steps
1: aq. NaHCO3 / 9 h / 0 - 20 °C
2: 1.) Cu(OAc)2*H2O, 2.) Pb(OAc)4 / 1.) toluene, Py, RT, 2 h, 2.) toluene, Py, from 80 deg C to 90 deg C, 12 h
3: 1.) n-BuLi / 1.) THF, -78 deg C, 2h, 2.) THF, a) -78 deg C, 2 h, b) RT, 6 h
4: 98 percent / H2, AcOH / 5percent Pd/C / ethyl acetate / 24 h / 45 °C / 57000 Torr
5: 1.) LDA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C
6: 1.) LDA, 2.) aq. NH4Cl / 1.) THF, hexane, -78 deg C, 2 h, 2.) THF, hexane
With
lead(IV) acetate; n-butyllithium; copper diacetate; hydrogen; sodium hydrogencarbonate; ammonium chloride; acetic acid; lithium diisopropyl amide;
palladium on activated charcoal;
In
ethyl acetate;
DOI:10.1016/0957-4166(96)00278-9