Multi-step reaction with 11 steps
1.1: triethylamine / tetrahydrofuran / 1.25 h / -78 - 0 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; diethyl ether / 0.67 h / -78 °C / Inert atmosphere
2.2: 2.25 h / -78 - 20 °C / Inert atmosphere
2.3: Inert atmosphere
3.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.2 h / -78 °C / Inert atmosphere
3.2: 6 h / -78 - 20 °C / Inert atmosphere
4.1: lithium hydroxide monohydrate; dihydrogen peroxide / tetrahydrofuran; water / 4 h / 0 - 20 °C / Inert atmosphere
4.2: pH 2 - 3 / Inert atmosphere
5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 10 h / 20 °C / Inert atmosphere
6.1: tetrahydrofuran; diethyl ether / 3 h / 0 °C / Inert atmosphere
6.2: Inert atmosphere
7.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / 20 °C / Inert atmosphere
7.2: 4 h / 20 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere
9.1: Dess-Martin periodane / dichloromethane / 3 h / 0 °C / Inert atmosphere
10.1: potassium hydroxide / ethanol; water / 48 h / 20 °C / Inert atmosphere
11.1: hydrogenchloride; water / methanol / 5 h / 20 °C / Inert atmosphere
With
hydrogenchloride; n-butyllithium; lithium hydroxide monohydrate; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; sodium hexamethyldisilazane; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water;
7.2: Wittig reaction / 10.1: Claisen-Schmidt condensation;
DOI:10.1007/s12272-011-0805-9