Multi-step reaction with 10 steps
1: 89 percent / I2; DMAP / CH2Cl2 / 5 h / 20 °C
2: 100 percent / Pd2(dba)3*CHCl3; Ph3As; CuI / dimethylformamide / 48 h / 20 °C
3: 100 percent / N,N-diisopropylethylamine / CH2Cl2 / 24 h / 20 °C
4: 100 percent / 3HF*Et3N / tetrahydrofuran / 50 h / 20 °C
5: N,N-diisoropylethylamine / CH2Cl2 / 0.5 h / -78 °C
6: N,N-diisoropylethylamine / CH2Cl2 / 1 h / -78 °C
7: 10.0 mg / Zn; aq. NH4Cl / methanol / 2 h / 20 °C
8: 86 percent / 4 Angstroem molecular sieves; DMTSF / CH2Cl2 / 2 h / 20 °C
9: 6 percent / NaBH3CN; TiCl4 / CH2Cl2; tetrahydrofuran / 1 h / -78 °C
With
dmap; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; copper(l) iodide; triphenyl-arsane; 4 A molecular sieve; iodine; titanium tetrachloride; sodium cyanoborohydride; ammonium chloride; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; zinc;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
3: Stille coupling;
DOI:10.1016/j.tet.2004.06.141