Multi-step reaction with 10 steps
1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C
1.2: 0.5 h / -78 °C
2.1: dichloromethane / 20 h / 20 °C
2.2: 0.5 h / 20 °C
3.1: sodium dithionite dihydrate / dichloromethane; water / 1 h / 20 °C / Inert atmosphere
4.1: triethylamine / dichloromethane / 2.5 h / 0 - 20 °C / Inert atmosphere
5.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere
5.2: 20 °C / Inert atmosphere
6.1: potassium hydroxide / methanol / 3 h / 50 °C / Inert atmosphere
6.2: 20 °C / pH 5 - 6 / Inert atmosphere
7.1: triethylamine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
8.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene / 1,4-dioxane / 7 h / 100 °C / Inert atmosphere
9.1: sodium periodate / tetrahydrofuran; water / 0.5 h / 20 °C
9.2: 12 h / 20 °C
10.1: C22H29O3P; palladium diacetate; potassium phosphate / water; toluene / 30 - 35 °C / Inert atmosphere
With
1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; sodium periodate; sodium dithionite dihydrate; C22H29O3P; potassium acetate; palladium diacetate; sodium hydride; triethylamine; potassium hydroxide; lithium diisopropyl amide;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
2.1: |Diels-Alder Cycloaddition / 2.2: |Diels-Alder Cycloaddition / 8.1: |Suzuki-Miyaura Coupling / 10.1: |Suzuki-Miyaura Coupling;
DOI:10.1021/ja409669r