Multi-step reaction with 12 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere
2.1: pyridinium p-toluenesulfonate / dichloromethane / 20 °C / Inert atmosphere
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere
3.2: 8 h / 0 - 20 °C / Inert atmosphere
4.1: pyridinium p-toluenesulfonate / methanol / 20 °C / Inert atmosphere
5.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane / 3 h / 0 °C / Inert atmosphere
5.2: 3 h / 20 °C / Inert atmosphere
6.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere
7.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere
8.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C / Inert atmosphere
9.1: titanium tetrachloride / dichloromethane / 0.08 h / 0 °C / Inert atmosphere
9.2: 0.33 h / Inert atmosphere
9.3: 0.67 h / -78 °C / Inert atmosphere
10.1: sodium tetrahydroborate / methanol / 20 °C / Inert atmosphere
11.1: pyridine / dichloromethane / 0 °C / Inert atmosphere
12.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere
With
pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; nickel(II) chloride hexahydrate; [bis(acetoxy)iodo]benzene; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; toluene; mineral oil;
9.3: |Evans Aldol Reaction;
DOI:10.1016/j.tetlet.2014.05.020