Multi-step reaction with 12 steps
1.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere
1.2: 24 h / 20 °C
2.1: 1H-imidazole / dichloromethane; toluene / 1 h / 20 °C / Inert atmosphere
3.1: sodium periodate; silica gel / ruthenium(III) trichloride hydrate / dichloromethane / 20 °C / Darkness; Inert atmosphere
4.1: dichloromethane; toluene / 0.75 h / 0 °C / Inert atmosphere
5.1: manganese(IV) oxide / acetonitrile / 20 °C / Inert atmosphere
6.1: dichloromethane; toluene / 1.5 h / 0 °C / Inert atmosphere
7.1: silver(l) oxide / dichloromethane / 40 °C / Inert atmosphere; Darkness
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere
9.1: dmap; triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h / 50 °C
11.1: ammonium chloride; iron / ethanol; water / 0.5 h / 85 °C / Inert atmosphere
12.1: dmap; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
12.2: 20 °C
With
1H-imidazole; dmap; manganese(IV) oxide; sodium periodate; tetrabutyl ammonium fluoride; silica gel; iron; diisobutylaluminium hydride; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; silver(l) oxide;
ruthenium(III) trichloride hydrate;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;