Multi-step reaction with 12 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere
2.1: thionyl chloride; pyridine / dichloromethane / 0.05 h / 0 °C
3.1: H3N*FH*3H2O / methanol / 12 h / Inert atmosphere; Reflux
4.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
5.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C / Inert atmosphere
5.2: 1 h / -78 °C / Inert atmosphere
6.1: dipyridine chromium trioxide / dichloromethane / 0 - 20 °C
7.1: samarium diiodide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
8.1: ammonium fluoride-hydrogen fluoride / methanol / 48 h / Inert atmosphere; Reflux
9.1: 2,6-dimethylpyridine / dichloromethane / -78 - 0 °C / Inert atmosphere
10.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / -78 - 20 °C / Inert atmosphere
10.2: Inert atmosphere
11.1: water; methanesulfonamide; AD-mix-β / tert-butyl alcohol / 48 h / 0 °C
12.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / Inert atmosphere
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; thionyl chloride; samarium diiodide; ammonium fluoride-hydrogen fluoride; methanesulfonamide; AD-mix-β; H3N*FH*3H2O; water; dipyridine chromium trioxide; Dess-Martin periodane; 9-bora-bicyclo[3.3.1]nonane;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
10.2: |Suzuki-Miyaura Coupling;
DOI:10.1002/anie.201203406