Multi-step reaction with 10 steps
1.1: pyridinium p-toluenesulfonate / methanol; dichloromethane / 3.5 h / 20 °C / Inert atmosphere
2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere
3.2: 1.75 h / -78 - 20 °C / Inert atmosphere
4.1: tetrahydrofuran / 2.5 h / 20 °C / Inert atmosphere
5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; caesium carbonate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
6.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
6.2: 1 h / 0 - 20 °C / Inert atmosphere
7.1: 2,6-dimethylpyridine / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
9.1: hydrogen / ethyl acetate / 14 h / 20 °C
10.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 2.5 h / 20 °C / pH 7 / aq. buffer
With
2,6-dimethylpyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; triphenyl-arsane; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; caesium carbonate; Dess-Martin periodane; acetic acid;
In
tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
2.1: Dess-Martin oxidation / 3.1: Wittig reaction / 3.2: Wittig reaction / 5.1: Suzuki coupling;
DOI:10.1002/anie.201108594