Multi-step reaction with 14 steps
1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; potassium acetate / tetrahydrofuran / 22 h / 68 °C
2.1: trimethylsilyl bromide
3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane
4.1: tetrahydrofuran / -78 °C
5.1: water / 90 °C
6.1: carbonochloridic acid 1-chloro-ethyl ester / toluene / Reflux
6.2: Reflux
7.1: triethylamine / dichloromethane
8.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,2-dimethoxyethane / 80 °C
9.1: ozone / methanol / -78 °C
10.1: potassium permanganate / acetone
11.1: hydrogenchloride / Reflux
12.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane
13.1: lithium hydroxide; water / tetrahydrofuran; methanol / 100 °C
14.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane
With
hydrogenchloride; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium permanganate; tetrakis(triphenylphosphine) palladium(0); oxalyl dichloride; trimethylsilyl bromide; carbonochloridic acid 1-chloro-ethyl ester; water; potassium acetate; sodium tris(acetoxy)borohydride; potassium carbonate; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N,N-dimethyl-formamide; lithium hydroxide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; 1,2-dichloro-ethane; acetone; toluene;
8.1: |Suzuki Coupling;
DOI:10.1016/j.bmcl.2014.05.036