Multi-step reaction with 9 steps
1.1: manganese(IV) oxide / dichloromethane / 1 h / Reflux
2.1: hydrazine hydrate; potassium hydroxide / 2,2'-[1,2-ethanediylbis(oxy)]bisethanol / 0.5 h / 160 - 180 °C
3.1: boron tribromide / dichloromethane / 2 h / -70 - 20 °C
3.2: 0 °C
4.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C
4.2: 0 °C
5.1: n-butyllithium / tetrahydrofuran / 0.33 h / -70 °C
5.2: 0.83 h / -70 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C
7.1: pyridine / 1 h / 0 °C
8.1: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine / N,N-dimethyl-formamide / 14 h / 70 °C / 760.05 Torr
9.1: methanol; sodium hydroxide / tetrahydrofuran / 2 h / 60 °C
9.2: 0 °C
With
pyridine; 1H-imidazole; methanol; manganese(IV) oxide; 1,1'-bis-(diphenylphosphino)ferrocene; n-butyllithium; tetrabutyl ammonium fluoride; palladium diacetate; boron tribromide; hydrazine hydrate; triethylamine; potassium hydroxide; sodium hydroxide;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol;
2.1: Wolff-Kishner reduction;
DOI:10.1016/j.bmc.2011.01.017