Multi-step reaction with 10 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C
1.2: 0 - 23 °C
2.1: sulfuric acid / 2.5 h / 50 °C
3.1: titanium tetrachloride / dichloromethane / 0.33 h / 0 °C
3.2: 1.25 h / 0 °C
4.1: 1H-imidazole; triethylsilyl chloride / dichloromethane / 16 h
4.2: 0.5 h / -78 °C
4.3: 20 °C
5.1: Dess-Martin periodane / dichloromethane / 1.5 h
6.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; toluene; ethanol / 2 h / 20 °C
7.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / toluene / 1.25 h / -40 °C
8.1: perchloric acid / water / 3 h
9.1: tetrakis(triphenylphosphine) palladium(0); triethylamine; copper(l) iodide / tetrahydrofuran / 1 h / 70 °C
10.1: water; sodium hydroxide / tetrahydrofuran; water; methanol / 2 h / 60 °C
With
1H-imidazole; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); perchloric acid; triethylsilyl chloride; sulfuric acid; water; titanium tetrachloride; sodium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; mineral oil;