Multi-step reaction with 10 steps
1.1: ethylmagnesium bromide; lithium chloride / tetrahydrofuran; diethyl ether / 20 °C / Inert atmosphere
1.2: 12 h / 20 °C / Inert atmosphere
2.1: water; calcium carbonate; methyl iodide / acetonitrile / 40 °C / Inert atmosphere
3.1: samarium diiodide / tetrahydrofuran; methanol / 0 °C / Inert atmosphere
4.1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 20 °C / Inert atmosphere
5.1: methanol; potassium carbonate / 20 °C / Inert atmosphere
6.1: 2,6-dimethylpyridine / dichloromethane / 0 °C / Inert atmosphere
7.1: pyridine; trifluoroacetic anhydride / acetonitrile / 0 °C / Inert atmosphere
7.2: 0 - 20 °C / Inert atmosphere
8.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
8.2: 1 h / 0 °C / Inert atmosphere
9.1: mercury(II) diacetate; water / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
9.2: Inert atmosphere
10.1: n-butyllithium / diethyl ether; pentane / 1.17 h / -80 °C / Inert atmosphere
10.2: -80 - 20 °C / Inert atmosphere
10.3: Inert atmosphere
With
pyridine; 2,6-dimethylpyridine; methanol; n-butyllithium; samarium diiodide; di-isopropyl azodicarboxylate; ethylmagnesium bromide; potassium tert-butylate; mercury(II) diacetate; water; potassium carbonate; triphenylphosphine; trifluoroacetic anhydride; calcium carbonate; lithium chloride; methyl iodide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; pentane;
4.1: Mitsunobu reaction / 7.1: Pummerer rearrangement / 8.2: Wittig reaction;
DOI:10.1016/j.tet.2011.09.011