Multi-step reaction with 10 steps
1.1: potassium carbonate / methanol / 3 h / 0 °C / Inert atmosphere
2.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere
3.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethyl acetate / 6.5 h / 20 °C
4.1: dmap / dichloromethane / 1 h / 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
5.2: Inert atmosphere
6.1: tributylphosphine; diamide / toluene / 2.5 h / 0 - 20 °C / Inert atmosphere
7.1: dilithium tetrabromonickelate(II) / tetrahydrofuran; toluene / 18.5 h / 0 °C / Inert atmosphere
8.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 0 °C / Inert atmosphere
9.1: N,N,N,N,N,N-hexamethylphosphoric triamide; phenyllithium; phenylmagnesium bromide / tetrahydrofuran; diethyl ether; hexane / 0.5 h / -78 - 0 °C / Inert atmosphere
10.1: diisobutylaluminium hydride / hexane; dichloromethane / 1 h / -78 °C / Inert atmosphere
10.2: 1 h / -78 - 20 °C / Inert atmosphere
With
1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; tributylphosphine; dilithium tetrabromonickelate(II); diamide; 10 wt% Pd(OH)2 on carbon; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; potassium carbonate; phenyllithium; phenylmagnesium bromide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
6.1: |Mitsunobu Displacement;
DOI:10.1246/cl.2009.934