Multi-step reaction with 11 steps
1.1: triethylamine / diethyl ether / 3 h / 20 °C
2.1: trifluoroacetic acid; N-iodo-succinimide / 3.5 h / 20 °C
3.1: N,N,N,N,N,N-hexamethylphosphoric triamide / copper(l) iodide / N,N-dimethyl-formamide / 20 - 80 °C
4.1: lithium hydroxide monohydrate / water; methanol / 0.5 h / 20 °C
4.2: pH 1
5.1: diazomethyl-trimethyl-silane / dichloromethane; diethyl ether / 20 °C
6.1: lithium diisopropyl amide / tetrahydrofuran / 0.37 h / 0 °C
6.2: 0.58 h / 0 °C
6.3: 20 °C
7.1: tert.-butylhydroperoxide / copper(l) iodide / N,N-dimethyl-formamide; acetonitrile / 20 - 50 °C
8.1: diethylamino-sulfur trifluoride / 1,2-dichloro-ethane / 24 h / 20 - 60 °C
9.1: boron tribromide / dichloromethane / 0 - 20 °C
10.1: pyridine / 0 - 20 °C
11.1: lithium chloride / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 20 - 100 °C
With
pyridine; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; N-iodo-succinimide; lithium hydroxide monohydrate; diethylamino-sulfur trifluoride; boron tribromide; triethylamine; trifluoroacetic acid; lithium chloride; lithium diisopropyl amide; diazomethyl-trimethyl-silane;
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;