Multi-step reaction with 13 steps
1.1: pyridine; potassium permanganate / water / 1 h / Reflux
2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C
3.1: aluminum (III) chloride / dichloromethane / 0.17 h / 25 °C
3.2: 25 °C
4.1: sodium tetrahydroborate; trifluoroacetic acid / dichloromethane / 0 - 25 °C / Inert atmosphere
5.1: caesium carbonate / tetrahydrofuran; methanol / 2 h / 70 °C
6.1: ozone / N,N-dimethyl-formamide / 0.13 h / -5 °C
7.1: hydrogenchloride / acetone / 24 h
8.1: hydrogenchloride / water / 24 h
9.1: potassium acetate / ethanol / 5 h / Reflux
10.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 15 h / 140 °C
11.1: hydrogen / nickel / tetrahydrofuran / 25 °C / 760.05 Torr
12.1: potassium acetate / toluene
13.1: isopentyl nitrite / toluene / 18 h / 80 °C
With
pyridine; hydrogenchloride; aluminum (III) chloride; sodium tetrahydroborate; potassium permanganate; oxalyl dichloride; hydrogen; potassium acetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; ozone; N,N-dimethyl-formamide; trifluoroacetic acid; isopentyl nitrite;
tris-(dibenzylideneacetone)dipalladium(0); nickel;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;