Multi-step reaction with 9 steps
1: 86 percent / 1.) NaH, 2.) n-Bu4NI / tetrahydrofuran / 24 h / 0 °C
2: 95 percent / 3M HCl / ethyl acetate / 1 h / Ambient temperature
3: 97 percent / NaBH(OAc)3 / 1,2-dichloro-ethane / Ambient temperature
4: 94 percent / 4M HCl / tetrahydrofuran / 3 h / Ambient temperature
5: 85 percent / pyridine / 24 h / 0 °C
6: 99 percent / K2CO3 / H2O; dimethylformamide / 24 h / Ambient temperature
7: 1.) Ti(Oi-Pr)4, 2.) KHMDS / 1.) THF, -78 deg C, 10 min, 2.) -70 deg C, 2 h
8: 95 percent / H2 / Pd/C / methanol / Ambient temperature
9: 96 percent / 6percent Na-Hg, Na2HPO4 / methanol / 2 h / 0 °C
With
pyridine; titanium(IV) isopropylate; hydrogenchloride; disodium hydrogenphosphate; sodium amalgam; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(98)01171-X