Multi-step reaction with 12 steps
1: norborn-2-ene; potassium carbonate; palladium diacetate / N,N-dimethyl acetamide / 16 h / 70 °C / Inert atmosphere
2: triethylamine; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere
3: toluene-4-sulfonic acid / methanol / 14 h / 20 °C / Inert atmosphere
4: 1H-imidazole; triphenylphosphine; iodine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
5: potassium carbonate / N,N-dimethyl-formamide / 3 h / 50 °C / Inert atmosphere
6: tris-(dibenzylideneacetone)dipalladium(0); (S)-2-(2-(bis(4-trifluoromethyl-phenyl)-phosphino))-5-(4-trifluoromethyl-phenyl)-4-tert-butyl-4,5-dihydro-oxazole / tert-butyl methyl ether / 15 h / 40 °C / Inert atmosphere
7: potassium hydroxide / methanol / 3.5 h / Inert atmosphere; Reflux
8: trichlorophosphate / toluene / 0.5 h / Inert atmosphere; Reflux
9: sodium tetrahydroborate / methanol / 3 h / 0 °C / Inert atmosphere
10: triethylamine; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere
11: sodium carbonate / dichloromethane / 12 h / 20 °C / Inert atmosphere
12: cerium(III) chloride heptahydrate; sodium periodate; ruthenium trichloride / ethyl acetate; water; acetonitrile / 0.25 h / 0 °C / Inert atmosphere
With
1H-imidazole; norborn-2-ene; dmap; (S)-2-(2-(bis(4-trifluoromethyl-phenyl)-phosphino))-5-(4-trifluoromethyl-phenyl)-4-tert-butyl-4,5-dihydro-oxazole; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; tris-(dibenzylideneacetone)dipalladium(0); cerium(III) chloride heptahydrate; iodine; palladium diacetate; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; potassium hydroxide; trichlorophosphate;
In
methanol; dichloromethane; tert-butyl methyl ether; N,N-dimethyl acetamide; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
8: |Bischler-Napieralski Reaction;
DOI:10.1039/c4cc01843e