Multi-step reaction with 11 steps
1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 20 °C
2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.75 h / -78 °C
3.1: tetrakis(triphenylphosphine) palladium(0); triethylamine / N,N-dimethyl-formamide / 0.67 h / 50 °C
4.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.75 h / -78 °C / Inert atmosphere
5.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C
6.1: tetrahydrofuran / 0.83 h / 20 °C
7.1: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C
9.1: camphor-10-sulfonic acid / methanol; dichloromethane / 5 h / 0 °C
10.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 1 h / 0 °C
11.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C
11.2: 2 h / -78 - 0 °C
With
1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrakis(triphenylphosphine) palladium(0); 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; camphor-10-sulfonic acid; potassium tert-butylate; dihydrogen peroxide; sulfur trioxide pyridine complex; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; sodium hydroxide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja305864z