Multi-step reaction with 13 steps
1.1: N,N-dimethyl-formamide / 20 h / 60 °C
2.1: acetic acid; Iodine monochloride / 3.67 h / 60 °C
3.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
5.1: diisobutylaluminium hydride / toluene / 3 h / 0 °C
6.1: 1H-imidazole / dichloromethane; N,N-dimethyl-formamide / 0 - 20 °C
7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C
8.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / tetrahydrofuran / 8 h / 65 °C / Inert atmosphere
9.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C
10.1: caesium carbonate / tetrahydrofuran; methanol / 4 h / 20 °C
11.1: tetra-(n-butyl)ammonium iodide; sodium hydroxide / dichloromethane; water; toluene / 20 h / 20 °C
12.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
12.2: 0.75 h / 20 °C
13.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C / 760.05 Torr
With
1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; Iodine monochloride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; sodium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;