Multi-step reaction with 9 steps
1.1: magnesium / tetrahydrofuran / 1 h / Inert atmosphere; Heating
1.2: 1.5 h / 0 °C / Inert atmosphere
2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / diethyl ether / 5 h / -30 - -5 °C / Inert atmosphere
2.2: 14 h / 20 °C / Inert atmosphere
3.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / diethyl ether / 2 h / -78 - -40 °C / Inert atmosphere
3.2: 14 h / -78 - -40 °C / Inert atmosphere
4.1: hydrogenchloride / ethanol; water / 2.5 h / 50 °C / Inert atmosphere
5.1: toluene-4-sulfonic acid / toluene / 0.5 h / Inert atmosphere; Reflux
6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 °C / Inert atmosphere
7.1: tert.-butyl lithium / diethyl ether; pentane / 1 h / -78 °C / Inert atmosphere
7.2: 0.25 h / -78 °C / Inert atmosphere
7.3: -78 °C / Inert atmosphere
8.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 750.08 Torr
9.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 - 40 °C / Inert atmosphere
With
hydrogenchloride; dmap; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; palladium 10% on activated carbon; hydrogen; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; magnesium; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; toluene; pentane;
1.2: Kumada coupling reaction / 6.1: Dess-Martin oxidation;
DOI:10.1002/chem.201104042