Multi-step reaction with 13 steps
1.1: N,N-dimethyl-formamide / 18 h / 95 °C
2.1: sodium periodate / water; tetrahydrofuran / 6 h / 20 °C
3.1: titanium tetrachloride / dichloromethane; diethyl ether / 1 h / -78 - -50 °C
3.2: 1 h / -50 °C
4.1: Dess-Martin periodane / dichloromethane / 16 h
5.1: acetic acid; iron / 4 h
6.1: pyridine / 18 h / 20 °C
6.2: Cooling with ice
7.1: lithium hydroxide / water; tetrahydrofuran; methanol / 15 h / 20 °C
8.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 96 h / 110 °C
8.2: 15 h / 20 °C
9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h
10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 120 h / 20 °C
11.1: potassium acetate / tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 0.33 h / 135 °C / Microwave irradiation
12.1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane; water / 20 h / 120 °C
13.1: trifluoroacetic acid / dichloromethane
With
pyridine; sodium periodate; potassium acetate; titanium tetrachloride; iron; sodium carbonate; Dess-Martin periodane; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide;
tris-(dibenzylideneacetone)dipalladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; tricyclohexylphosphine;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;