Multi-step reaction with 11 steps
1.1: tetrabutylammomium bromide; palladium diacetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine / N,N-dimethyl-formamide / 20 - 100 °C / Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / 0 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.67 h / -78 °C / Inert atmosphere
4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / 0 °C / Inert atmosphere
4.2: -40 - 0 °C / Inert atmosphere
5.1: pyridine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere
5.2: 0.17 h / 0 °C / Inert atmosphere
6.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
7.1: sodium azide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 20 - 80 °C / Inert atmosphere
8.1: water; triphenylphosphine / tetrahydrofuran / 20 - 50 °C / Inert atmosphere
9.1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
10.1: water; potassium hydroxide / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere
11.1: pyridine / dichloromethane / -78 - 20 °C / Inert atmosphere
With
pyridine; dmap; sodium azide; tetrabutylammomium bromide; water; palladium diacetate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; potassium hydroxide;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
1.1: Heck reaction / 4.2: Wittig reaction;
DOI:10.1002/chem.201002287