Multi-step reaction with 11 steps
1.1: toluene / 3 h / 110 °C / Inert atmosphere
2.1: phosphorous acid trimethyl ester / 16 h / 111 °C / Inert atmosphere
3.1: hydrogenchloride / diethyl ether; dichloromethane / 0.25 h / 0 °C / Inert atmosphere
4.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 25 °C / Inert atmosphere
5.1: sodium hydrogencarbonate / 1,4-dioxane; water / 3.25 h / 0 - 25 °C
6.1: lithium hydroxide / tetrahydrofuran; water / 5 h / 0 - 25 °C
6.2: pH 3
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 17 h / 0 - 25 °C / Inert atmosphere
8.1: tris-(dibenzylideneacetone)dipalladium(0); diethylamine; 1,4-di(diphenylphosphino)-butane / tetrahydrofuran / 2.05 h / 25 °C / Inert atmosphere
9.1: sulfur; lithium hexamethyldisilazane / tetrahydrofuran; diethyl ether / 5 h / 25 °C / Inert atmosphere
10.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 5 h / 0 - 25 °C / Inert atmosphere
11.1: 1.3-propanedithiol; triethylamine / dichloromethane; acetonitrile / 0.5 h / 25 °C / Inert atmosphere
With
1.3-propanedithiol; hydrogenchloride; sulfur; dmap; tris-(dibenzylideneacetone)dipalladium(0); sodium hydrogencarbonate; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 1,4-di(diphenylphosphino)-butane; trifluoroacetic acid; lithium hydroxide; lithium hexamethyldisilazane; phosphorous acid trimethyl ester;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; toluene; acetonitrile;
DOI:10.1021/ja308429f