Multi-step reaction with 11 steps
1.1: potassium carbonate / acetone / 2 h / Reflux; Inert atmosphere
2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C / Inert atmosphere
2.2: 16 h / 0 °C / Inert atmosphere
3.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere
3.2: 0 - 20 °C / Inert atmosphere
4.1: methanesulfonamide; AD-mix β / water; tert-butyl alcohol / 3.8 h / 0 °C / Inert atmosphere
5.1: pyridine / dichloromethane / 29 h / 0 - 20 °C / Inert atmosphere
6.1: potassium carbonate / methanol / 3 h / 0 °C / Inert atmosphere
7.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere
8.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethyl acetate / 6.5 h / 20 °C
9.1: dmap / dichloromethane / 1 h / 20 °C / Inert atmosphere
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
10.2: Inert atmosphere
11.1: tributylphosphine; diamide / toluene / 2.5 h / 0 - 20 °C / Inert atmosphere
With
pyridine; 1H-imidazole; dmap; tributylphosphine; methanesulfonamide; diamide; AD-mix β; 10 wt% Pd(OH)2 on carbon; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; mineral oil; tert-butyl alcohol;
11.1: |Mitsunobu Displacement;
DOI:10.1246/cl.2009.934