Multi-step reaction with 11 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere
1.2: 2 h / -78 °C / Inert atmosphere
2.1: pyridinium p-toluenesulfonate / ethanol / 25 h / 23 °C / Inert atmosphere
3.1: triethylamine / dichloromethane; dimethyl sulfoxide / 0.17 h / 0 °C / Inert atmosphere
3.2: 2 h / 0 °C / Inert atmosphere
4.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.25 h / -78 °C / Inert atmosphere
4.2: 2 h / -78 °C / Inert atmosphere
5.1: hydrogenchloride / methanol; water / 6 h / 23 °C / Inert atmosphere
6.1: copper(I) thiophene-2-carboxylate / 1-methyl-pyrrolidin-2-one / 0 - 23 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 23 °C / Inert atmosphere
8.1: dichloromethane / 0.5 h / 0 °C / Inert atmosphere
8.2: 0.5 h / 0 °C / Inert atmosphere
9.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 3 h / 23 °C / Inert atmosphere
10.1: 1H-imidazole / dichloromethane / 18 h / 23 °C / Inert atmosphere
11.1: triethylamine; dmap / dichloromethane / 5 h / 23 °C / Inert atmosphere
With
1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; copper(I) thiophene-2-carboxylate; 18-crown-6 ether; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; triethylamine;
In
tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; toluene;
4.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1021/ja404578u