Multi-step reaction with 10 steps
1.1: diisobutylaluminium hydride / dichloromethane / 0.33 h / -78 °C / Inert atmosphere
2.1: triethylamine; dmap / 0 - 20 °C / Inert atmosphere
3.1: caesium carbonate; copper(l) iodide; N,N`-dimethylethylenediamine / 1,4-dioxane / 24 h / 70 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 20 °C / Inert atmosphere
5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
6.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate dihydrate; sodium chlorite / tert-butyl alcohol; water / 20 °C / Inert atmosphere
7.1: caesium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
8.1: triethylamine; dmap / 2.5 h / 0 - 20 °C / Inert atmosphere
9.1: 2-methyl-but-2-ene; morpholine; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 1.5 h / -5 °C / Inert atmosphere
9.2: Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
With
morpholine; dmap; sodium chlorite; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; N,N`-dimethylethylenediamine;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja401457h