Multi-step reaction with 9 steps
1.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tert-butyl methyl ether / 0.5 h / 0 - 20 °C / Inert atmosphere
1.2: 6.5 h / 0 - 20 °C / Inert atmosphere
2.1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C / Inert atmosphere
2.2: 20 °C / Inert atmosphere
3.1: phosphorus tribromide / diethyl ether / 0.08 h / 0 °C / Inert atmosphere
4.1: potassium carbonate; potassium iodide / tetrahydrofuran; water / 24 h / 20 °C / Inert atmosphere
5.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere
5.2: 12 h / 20 °C / Inert atmosphere
6.1: cerium(III) chloride / tetrahydrofuran; diethyl ether / 13 h / 20 °C / Inert atmosphere
6.2: 20 °C / Inert atmosphere
7.1: titanium tetrachloride / dichloromethane / 0.83 h / -78 - 20 °C / Inert atmosphere
7.2: 20 °C / Inert atmosphere
8.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere
9.1: pyridine / dichloromethane / Inert atmosphere
9.2: 72 h / 20 °C / Inert atmosphere
With
pyridine; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; N,N,N,N,-tetramethylethylenediamine; dimethylsulfide borane complex; phosphorus tribromide; titanium tetrachloride; sodium hydride; potassium carbonate; potassium iodide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; tert-butyl methyl ether; water; N,N-dimethyl-formamide;
6.1: Grignard reaction;
DOI:10.1016/j.tet.2011.09.072