Multi-step reaction with 12 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -20 °C / Inert atmosphere
1.2: 1 h / -20 °C / Inert atmosphere
2.1: ethylmagnesium bromide; lithium chloride / tetrahydrofuran; diethyl ether / 24 h / 20 °C / Inert atmosphere
3.1: water; calcium carbonate; methyl iodide / acetonitrile / 15 h / 40 °C / Inert atmosphere
4.1: samarium diiodide / tetrahydrofuran; methanol / 0.5 h / -10 °C / Inert atmosphere
5.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
6.1: potassium carbonate / tetrahydrofuran; methanol / 0.5 h / 0 °C / Inert atmosphere
7.1: 1H-imidazole; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere
8.1: pyridine / acetonitrile / 0.5 h / 0 °C / Inert atmosphere
9.1: water; potassium acetate / acetonitrile / 12 h / 0 °C / Inert atmosphere
10.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere
10.2: 2 h / -78 °C / Inert atmosphere
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
12.1: dmap; camphor-10-sulfonic acid; dicyclohexyl-carbodiimide / dichloromethane / 15 h / 30 °C
With
pyridine; 1H-imidazole; dmap; n-butyllithium; samarium diiodide; camphor-10-sulfonic acid; ethylmagnesium bromide; tetrabutyl ammonium fluoride; water; tert.-butyl lithium; potassium acetate; potassium carbonate; dicyclohexyl-carbodiimide; triphenylphosphine; calcium carbonate; lithium chloride; diethylazodicarboxylate; methyl iodide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetonitrile; pentane;
5.1: Mitsunobu reaction / 8.1: Pummerer rearrangement;
DOI:10.1021/ol2007296