Multi-step reaction with 11 steps
1.1: cyanomethylenetributyl-phosphorane / toluene / 1 h / 100 °C
2.1: 0.1 h / 230 °C
3.1: cyanomethylenetributyl-phosphorane / toluene / 1 h / 110 °C
4.1: dmap / acetonitrile / 20 °C
5.1: palladium diacetate / 4 h / 20 °C
6.1: 2,6-dimethylpyridine; osmium(VIII) oxide; sodium periodate / water; 1,4-dioxane / 1 h / 0 - 20 °C
7.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere
7.2: 0.5 h / -78 °C
8.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C
9.1: potassium carbonate; isopropyl alcohol / 2 h / 65 °C
10.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C
10.2: 1 h
11.1: titanium tetrachloride / dichloromethane / 0.25 h / 0 - 20 °C
11.2: 16 h / -40 - 20 °C
With
2,6-dimethylpyridine; dmap; manganese(IV) oxide; sodium periodate; osmium(VIII) oxide; palladium diacetate; titanium tetrachloride; sodium hydride; potassium carbonate; isopropyl alcohol; cyanomethylenetributyl-phosphorane; lithium diisopropyl amide;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;