Multi-step reaction with 7 steps
1.1: toluene-4-sulfonic acid / methanol / 2 h / Heating / reflux
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 17 h / 0 - 25 °C
3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 2.5 h / 0 - 25 °C
4.1: n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane / tetrahydrofuran; hexanes / 0.83 h / -78 - 0 °C / Cooling with acetone-dry ice
4.2: 21 h / -78 - 0 °C
5.1: sulfuric acid; water / 1,4-dioxane / 19.5 h / 25 °C / Heating / reflux
6.1: sodium periodate / methanol; water / 6 h / 25 °C
7.1: potassium permanganate / methanol; water / 3 h / 0 - 25 °C
With
1H-imidazole; potassium permanganate; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; sulfuric acid; water; iodine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane;
toluene-4-sulfonic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexanes; dichloromethane; water;