Multi-step reaction with 8 steps
1: 1.) n-butyllithium / 1.) THF, hexane, 0 deg C, 1 h, 2.) -78 -> 0 deg C
2: 85 percent / Zn activated by copper acetate / methanol; H2O / 12 h
3: 1.63 g / pyridine / 12 h
4: 76 percent / Na2HPO4, 6percent Na(Hg) / tetrahydrofuran; methanol / 4 h
5: 81 percent / TBAF / tetrahydrofuran / 12 h / Ambient temperature
6: 86 percent / CBr4, PPh3 / CH2Cl2 / 12 h
7: 1.) NaH, 2.) tetrabutylammonium fluoride / 1.) THF, r.t., 1 h, 2.) THF, 60 deg C, 2 h
8: 84 percent / DDQ / CH2Cl2; H2O / 1 h / Ambient temperature
With
disodium hydrogenphosphate; n-butyllithium; sodium amalgam; carbon tetrabromide; tetrabutyl ammonium fluoride; sodium hydride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; water;
DOI:10.1021/jo960134o