Multi-step reaction with 9 steps
1.1: diisobutylaluminium hydride / dichloromethane; cyclohexane / 1 h / -78 °C / Inert atmosphere
1.2: 4 h / 20 °C / Cooling with ice
2.1: triethylamine / dichloromethane / 1 h / Cooling with ice
3.1: N,N,N,N,N,N-hexamethylphosphoric triamide; tert.-butyl lithium / tetrahydrofuran; pentane / 0.5 h / -78 - -40 °C / Inert atmosphere
4.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / -10 °C / Inert atmosphere
5.1: camphor-10-sulfonic acid / methanol; dichloromethane / 1 h / -10 °C
6.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 2 h / Cooling with ice; Inert atmosphere
7.1: 1-methyl-pyrrolidin-2-one; titanium tetrachloride; sparteine / dichloromethane / 2 h / -78 - 0 °C / Inert atmosphere
8.1: bis-[(trifluoroacetoxy)iodo]benzene / methanol; water / 0.08 h / Cooling with ice
9.1: hydrogen fluoride / water; acetonitrile / 0.5 h / 20 °C
With
1-methyl-pyrrolidin-2-one; N,N,N,N,N,N-hexamethylphosphoric triamide; camphor-10-sulfonic acid; hydrogen fluoride; tert.-butyl lithium; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; titanium tetrachloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; sparteine;
In
tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; acetonitrile; pentane;
DOI:10.1002/anie.201201395