Multi-step reaction with 9 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.03 h / Inert atmosphere; Cooling with ice
1.2: 0.33 h / 0 °C / Inert atmosphere
2.1: n-butyllithium; diisopropylamine / tetrahydrofuran; pentane / 0.23 h / -78 - 0 °C / Inert atmosphere
2.2: 0.77 h / -78 °C / Inert atmosphere
2.3: -78 °C
3.1: pyridinium p-toluenesulfonate / 3 h / 45 °C / Inert atmosphere
4.1: sodium tetrahydroborate; ethanol / 15 h / -15 °C / Inert atmosphere
5.1: 1H-imidazole / dichloromethane / 2 h / 20 °C / Inert atmosphere
6.1: magnesium / diethyl ether / Inert atmosphere; Reflux
6.2: 1.22 h / -78 °C / Inert atmosphere
6.3: 70 h / 20 °C / Inert atmosphere
7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.68 h / Inert atmosphere; Cooling with ice
8.1: lithium dihydronaphthylide radical / tetrahydrofuran / 1 h / -30 - -10 °C / Inert atmosphere
9.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; acetonitrile / 1.33 h / 20 °C / Inert atmosphere
9.2: 0.75 h / Inert atmosphere; Cooling with ice
With
1H-imidazole; sodium tetrahydroborate; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ethanol; [bis(acetoxy)iodo]benzene; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; lithium dihydronaphthylide radical; magnesium; diisopropylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; pentane;
DOI:10.1021/ja203034k