Multi-step reaction with 7 steps
1.1: sodium hydrogencarbonate / tetrahydrofuran; water / 15 h / 0 - 20 °C / Inert atmosphere
2.1: 1,1'-carbonyldiimidazole / dichloromethane / 0.25 h / 20 °C / Inert atmosphere
2.2: 15 h / 20 °C / Inert atmosphere
3.1: diethyl ether / 1 h / 0 °C / Inert atmosphere
4.1: potassium tert-butylate / diethyl ether / 0.5 h / 0 °C / Inert atmosphere
4.2: 2 h / Inert atmosphere
5.1: acetic acid / diethyl ether / 24 h / Inert atmosphere
6.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere
6.2: 15 h / Inert atmosphere
7.1: sodium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 12 h / 120 °C / Inert atmosphere
With
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium tert-butylate; sodium hydrogencarbonate; acetic acid; 1,1'-carbonyldiimidazole; sodium hydroxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water;
7.1: |Suzuki Coupling;
DOI:10.1021/ol400137q