Multi-step reaction with 8 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 / 2 h / 0 - 20 °C / Inert atmosphere
4.1: toluene / 5 h / 105 °C
5.1: dihydrogen peroxide; methyltrioxorhenium(VII) / dichloromethane / 20 °C
6.1: trichlorophosphate / 1,2-dichloro-ethane / 4 h / 70 °C / Inert atmosphere
7.1: trimethylsilyl bromide / propiononitrile / 3.5 h / 110 °C / Inert atmosphere
8.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 6 h / 80 °C / Inert atmosphere; Sealed tube
With
n-butyllithium; sodium azide; trimethylsilyl bromide; dihydrogen peroxide; titanium tetrachloride; methyltrioxorhenium(VII); caesium carbonate; triethylamine; diisopropylamine; trichlorophosphate;
tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; propiononitrile;