Multi-step reaction with 12 steps
1.1: sodium hydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux
2.1: palladium 10% on activated carbon; perchloric acid; hydrogen; acetic acid / 16 h
3.1: water; hydrogen bromide; acetic acid / 2 h / Inert atmosphere; Reflux
4.1: sulfuric acid / 1 h / Inert atmosphere; Reflux
5.1: pyridine / 0 - 20 °C / Inert atmosphere
6.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 16 h / Reflux; Inert atmosphere
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
8.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C
9.1: borane-THF / tetrahydrofuran / 1 h / 20 °C
9.2: 0.67 h / -78 °C
9.3: 2 h / -78 °C
10.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C
11.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C
12.1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16 h / Reflux; Inert atmosphere
With
pyridine; 1H-imidazole; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; perchloric acid; borane-THF; sulfuric acid; palladium 10% on activated carbon; water; hydrogen bromide; hydrogen; sodium hydride; sodium carbonate; Dess-Martin periodane; acetic acid;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
6.1: Suzuki coupling / 12.1: Stille coupling;
DOI:10.1021/jm101597x