Multi-step reaction with 9 steps
1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 18.75 h / -78 - -30 °C
1.2: 20 °C
2.1: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C
3.1: triethylamine; titanium tetrachloride / dichloromethane / 6.3 h / 0 - 20 °C / Inert atmosphere
4.1: toluene / 18 h / 105 °C
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 17.5 h / 0 - 20 °C
6.1: phosphorus(V) oxybromide / 1,2-dichloro-ethane / 4.5 h / 0 - 20 °C / Inert atmosphere
7.1: potassium phosphate; caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / toluene; water / 5 h / 70 °C / Inert atmosphere
8.1: trifluoroacetic acid / 3.5 h / 20 °C
9.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 0.42 h / 150 °C / Inert atmosphere; Microwave irradiation
With
potassium phosphate; n-butyllithium; sodium azide; titanium tetrachloride; caesium carbonate; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; phosphorus(V) oxybromide;
tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;