Multi-step reaction with 10 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
2.2: 4 h / -78 °C / Inert atmosphere
3.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; toluene / 24 h / 90 °C / Inert atmosphere
4.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere
5.1: pyridine; dmap / chloroform / 0 - 20 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
7.1: triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) / dichloromethane / 5 h / 20 °C / Inert atmosphere
8.1: methanol; 5%-palladium/activated carbon; hydrogen / 4 h
9.1: bromine / dichloromethane / 0 - 20 °C / Inert atmosphere
10.1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
With
pyridine; 1H-imidazole; methanol; dmap; potassium phosphate; n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; 5%-palladium/activated carbon; tetrabutyl ammonium fluoride; hydrogen; bromine; diisobutylaluminium hydride; triethylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0);
In
tetrahydrofuran; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;
3.1: Suzuki-Miyaura Cross Coupling / 7.1: Friedel Crafts alkylation;
DOI:10.1021/ol300770w