Multi-step reaction with 10 steps
1.1: ethanol / 3 h / -15 - 20 °C
2.1: periodic acid / iron(III) chloride / acetonitrile / 20 °C
3.1: magnesium oxide; [bis(acetoxy)iodo]benzene / dirhodium tetraacetate / dichloromethane / 16 h / 20 °C
4.1: potassium carbonate; methanol / 1 h / 20 °C
5.1: pyridine / 24 h / 20 °C
6.1: hydrogenchloride; titanium(III) chloride / water; tetrahydrofuran / 18 h / 20 °C
6.2: pH 8 / Cooling with ice
7.1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol; tetrahydrofuran / 3 h / -40 - 0 °C
8.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane / 1.33 h / 100 °C / Inert atmosphere
9.1: sodium ethanolate / ethanol / 7 h / 60 °C / Inert atmosphere
10.1: triethylamine / dichloromethane / 50 h / 0 °C
With
pyridine; hydrogenchloride; methanol; titanium(III) chloride; [bis(acetoxy)iodo]benzene; sodium ethanolate; magnesium oxide; potassium carbonate; periodic acid; triethylamine; N-ethyl-N,N-diisopropylamine;
iron(III) chloride; dirhodium tetraacetate; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; isopropyl alcohol; acetonitrile;