Multi-step reaction with 11 steps
1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0.5 h / 0 °C
2.1: triethylamine / dichloromethane / 1 h / 0 °C
3.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.33 h / -40 - 20 °C
4.1: titanium(IV) isopropylate / tetrahydrofuran / 6 h / 0 - 20 °C
5.1: dichloromethane; tetrahydrofuran / 2 h / -40 - 20 °C
6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -60 °C / Inert atmosphere
6.2: 1 h / -60 - 20 °C
7.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 4 h / Inert atmosphere; Reflux
8.1: palladium on activated charcoal; hydrogen / methanol / 24 h / 20 °C / 2585.81 Torr / Inert atmosphere
9.1: hydrogenchloride / methanol / 1 h / Inert atmosphere
10.1: triethylamine; dmap / ethyl acetate / 1.5 h / 0 °C
10.2: 48 h / 50 °C
11.1: ozone; oxygen / dichloromethane / -78 °C
11.2: 20 h / -78 - 20 °C / Inert atmosphere
With
titanium(IV) isopropylate; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium(0); oxalyl dichloride; palladium on activated charcoal; hydrogen; oxygen; diisobutylaluminium hydride; ozone; triethylamine; N,N-dimethyl-formamide; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;