Multi-step reaction with 12 steps
1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 2 h / 30 °C
2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 20 °C
3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3 h / 50 °C
4.1: n-butyllithium / tetrahydrofuran; pentane / 0.5 h / -78 °C / Inert atmosphere
4.2: 2 h / Inert atmosphere
5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3.5 h / 50 °C
6.1: palladium on activated charcoal; hydrogen / methanol; ethyl acetate / 12 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 0.08 h / -30 °C / Inert atmosphere
7.2: 3 h / 20 °C
8.1: N-chloro-succinimide / N,N-dimethyl-formamide / 3 h / 20 °C
9.1: boron tribromide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
10.1: potassium hydroxide / tetrahydrofuran; methanol / 0.25 h / 20 °C
11.1: N-ethyl-N,N-diisopropylamine; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 10 h / Inert atmosphere; Reflux
12.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 h / 20 °C
With
tris-(dibenzylideneacetone)dipalladium(0); N-chloro-succinimide; n-butyllithium; palladium on activated charcoal; tetrabutyl ammonium fluoride; hydrogen; boron tribromide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; pentane;