Multi-step reaction with 14 steps
1.1: titanium tetrachloride / tetrahydrofuran; dichloromethane / 1 h / -78 - -30 °C
2.1: manganese(IV) oxide / 1,4-dioxane / 17 h / Reflux
3.1: titanium(IV) tetraethanolate / tetrahydrofuran / 2.5 h / Reflux
3.2: Cooling with ice
4.1: cesium fluoride / tetrahydrofuran; hexane / 4 h / -50 - 0 °C
5.1: hydrogenchloride / toluene / 4 h / Reflux
6.1: diborane / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
7.1: potassium carbonate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 19 h / 0 °C / Inert atmosphere
8.1: potassium tert-butylate / tert-butyl alcohol / 0.5 h / 100 °C / Inert atmosphere
9.1: Lawessons reagent / 2 h / 80 °C
10.1: tert.-butylhydroperoxide; ammonium hydroxide; ammonia / methanol / 2 h / 20 °C
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere
12.1: hydrogen / Raney-Ni / methanol / 20 h / 1.5 °C
13.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere
14.1: hydrogenchloride / 1,4-dioxane / 24 h / 40 °C / Sealed vial
With
Lawessons reagent; hydrogenchloride; tert.-butylhydroperoxide; manganese(IV) oxide; ammonium hydroxide; potassium tert-butylate; ammonia; hydrogen; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; cesium fluoride; diborane;
titanium(IV) tetraethanolate; titanium tetrachloride;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;