Multi-step reaction with 12 steps
1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C
1.3: 4 h / 0 - 50 °C
2.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / -78 - 20 °C
2.2: 0 - 20 °C
3.1: 2-methyl-but-2-ene; water; sodium chlorite; sodium dihydrogenphosphate / tert-butyl alcohol / 0.5 h / 20 °C
3.2: pH 1
4.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 0.5 h / 20 °C
5.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C
6.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 19 h / Inert atmosphere; Reflux
7.1: ozone; oxygen / dichloromethane / -78 °C
7.2: -78 - 25 °C
8.1: bromine; acetic acid / 1 h / 20 °C
9.1: boron tribromide / dichloromethane / 1.5 h / -78 - 25 °C
10.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C
11.1: copper(l) iodide / N,N-dimethyl-formamide / 20 h / 100 °C / Sealed
12.1: sodium tetrahydroborate; methanol / 2 h
With
hydrogenchloride; methanol; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; copper(l) iodide; 2-methyl-but-2-ene; oxalyl dichloride; water; bromine; oxygen; boron tribromide; diisobutylaluminium hydride; potassium carbonate; ozone; acetic acid; triethylamine; sodium nitrite;
tetrakis(triphenylphosphine) palladium(0); N,N-dimethyl-formamide;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;