Multi-step reaction with 14 steps
1.1: pyridine / dichloromethane
2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine / propan-1-ol
3.1: potassium hydroxide
4.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 20 °C / Inert atmosphere
5.1: potassium carbonate / acetone
6.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 4 h / 45 °C / Inert atmosphere
7.1: sodium hydroxide; trimethylphosphane / tetrahydrofuran; water / 4 h
8.1: dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1 h / 0 °C / Inert atmosphere
8.2: 48 h / 20 °C / Inert atmosphere
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran
10.1: silver(l) oxide / dichloromethane / 0.25 h / Cooling with ice
10.2: 30 h / 20 °C
11.1: potassium hydroxide / ethanol
11.2: 1 h / 50 °C
12.1: sodium methylate / methanol / 40 °C
13.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 0 °C
14.1: methyl-phenyl-thioether; trifluoroacetic acid / dichloromethane / 1 h / 0 °C
With
pyridine; dmap; platinum(IV) oxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; Hoveyda-Grubbs catalyst second generation; methyl-phenyl-thioether; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; trifluoroacetic acid; potassium hydroxide; sodium hydroxide; silver(l) oxide; trimethylphosphane;
In
tetrahydrofuran; methanol; propan-1-ol; ethanol; dichloromethane; water; acetone; toluene;
4.1: Mitsunobu reaction;
DOI:10.1021/ol202528k