Multi-step reaction with 8 steps
1.1: potassium hydroxide / water / 20 °C
2.1: Jones reagent / 20 °C / Inert atmosphere
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; pyridine / N,N-dimethyl-formamide; dichloromethane / 37 h / 0 - 20 °C / Inert atmosphere
4.1: tetrahydrofuran; water / 4 h / 20 °C
5.1: N-Bromosuccinimide / dichloromethane / 2.5 h / 20 °C / Inert atmosphere
6.1: copper(l) iodide / 1,4-dioxane / 24 h / 90 °C / Inert atmosphere
7.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere
7.2: 0.33 h / -78 - 20 °C / Inert atmosphere
8.1: chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]-palladium / toluene; 1,4-dioxane / 48 h / 80 °C / Inert atmosphere
With
pyridine; N-Bromosuccinimide; copper(l) iodide; Jones reagent; n-butyllithium; chloro(2-dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]-palladium; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
2.1: |Jones Oxidation / 8.1: |Stille Cross Coupling;
DOI:10.1021/ol302121w