Multi-step reaction with 11 steps
1.1: diisobutylaluminium hydride / toluene / 2 h / -60 - -50 °C / Inert atmosphere
1.2: 0.5 h / -50 - 30 °C
2.1: manganese(IV) oxide / toluene / 24 h / 25 - 30 °C
3.1: lithium hexamethyldisilazane / hexane; tetrahydrofuran / 1 h / -35 - -15 °C
3.2: 1 h / -80 - -75 °C
4.1: sodium hydroxide; water / tetrahydrofuran / 24 h / 20 - 30 °C
4.2: pH 1.5 - 2
4.3: 20 °C
5.1: hydrogenchloride; water / dichloromethane / 0 - 30 °C / pH 2 - 2.5
6.1: potassium iodide / N,N-dimethyl-formamide / 0.75 h / 25 - 65 °C / Inert atmosphere
6.2: 0.5 h / 60 - 65 °C
6.3: 0.5 h / 60 - 65 °C
7.1: dichloromethane / 3.25 h / 15 - 20 °C
8.1: zinc(II) oxide / toluene / 2 h / 25 - 30 °C / Inert atmosphere
8.2: 12 h
9.1: hydrogenchloride; water / acetonitrile / 4 h / -10 °C
10.1: sodium tetrahydroborate; diethyl methoxy borane; methanol / ethyl acetate; tetrahydrofuran / 5 h / -80 - -75 °C / Inert atmosphere
11.1: sodium hydroxide; water / ethanol / 2 h / 0 - 5 °C
With
hydrogenchloride; methanol; manganese(IV) oxide; sodium tetrahydroborate; diethyl methoxy borane; water; diisobutylaluminium hydride; potassium iodide; zinc(II) oxide; sodium hydroxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;