Multi-step reaction with 12 steps
1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.25 h / -78 °C / Inert atmosphere
2.1: sodium hydride / tetrahydrofuran / 1 h / -78 - -40 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.25 h / -78 °C / Inert atmosphere
4.1: benzene / Inert atmosphere; Reflux
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
6.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0 - 20 °C / Inert atmosphere
7.1: lithium hexamethyldisilazane / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 0.25 h / -78 °C / Inert atmosphere
7.2: 3 h / -78 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; N,N-dimethyl-formamide; water / 12 h / 20 - 50 °C / Inert atmosphere
9.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1 h / 0 - 20 °C / Inert atmosphere
10.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0 °C / Inert atmosphere
10.2: 12 h / 20 °C / Inert atmosphere
11.1: lithium hydroxide; water / tetrahydrofuran; methanol / 1 h / 0 - 20 °C
12.1: 2-methyl-6-nitrobenzoic anhydride; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere
With
dmap; 2-methyl-6-nitrobenzoic anhydride; tetrabutyl ammonium fluoride; water; sulfur trioxide pyridine complex; sodium hydride; diisobutylaluminium hydride; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hydroxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
2.1: |Wittig-Horner Reaction / 4.1: |Wittig-Horner Reaction / 7.1: |Julia-Kocienski Olefination / 7.2: |Julia-Kocienski Olefination;
DOI:10.1039/c2ob26533h