Multi-step reaction with 11 steps
1: 95 percent / NaBH4 / propan-2-ol; H2O / 1 h / 0 °C
2: pyridine; CH2Cl2 / 24 h / Ambient temperature
3: Et3N / CH2Cl2 / 2 h / 0 °C
4: Et3N / pyridine; toluene / 24 h / 110 °C
5: TiCl4, PhSH / CH2Cl2 / 2 h / 0 °C
6: K2CO3 / methanol / 2 h / 0 °C
7: Et3N / 4-dimethylaminopyridine / CH2Cl2 / 2 h / 0 °C
8: 84 percent / CuBr / tetrahydrofuran / 4 h / -30 - 0 °C
9: 1.) NaI, Me3SiCl, 2.) POCl3 / 1.) CH3CN, H2O, 0 - 10 deg C, 2 h, 2.) pyridine, CH3CN, 0 - 15 deg C, 4 h
10: 4N HCl / tetrahydrofuran / 24 h / Ambient temperature
11: aq. NaOH / Ambient temperature
With
hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; chloro-trimethyl-silane; titanium tetrachloride; potassium carbonate; thiophenol; triethylamine; sodium iodide; copper(I) bromide; trichlorophosphate;
dmap;
In
tetrahydrofuran; pyridine; methanol; dichloromethane; water; isopropyl alcohol; toluene;
DOI:10.1016/S0040-4039(00)75806-0