Multi-step reaction with 14 steps
1: triethylamine / N,N-dimethyl-formamide / 20 - 25 °C
2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 20 - 25 °C
3: phosgene; dimethyl sulfoxide; triethylamine / dichloromethane / 20 - 25 °C
4: chromium dichloride; nickel dichloride / tetrahydrofuran / 20 - 25 °C
5: triphenylphosphine; diethylazodicarboxylate / 20 - 25 °C
6: potassium carbonate / methanol / 20 - 25 °C
7: triethylamine / dichloromethane / 0 °C
8: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 °C
9: triethylamine / acetonitrile / Reflux
10: toluene-4-sulfonic acid / methanol / 20 - 25 °C
11: 1H-imidazole / 20 - 25 °C
12: diphenylphosphoranyl azide; triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 20 - 25 °C
13: water; triphenylphosphine / Reflux
14: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 - 25 °C
With
1H-imidazole; chromium dichloride; phosgene; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; water; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; nickel dichloride; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
4: Nozaki-Hiyama-Kishi coupling / 5: Mitsunobu inversion;
DOI:10.1021/ja108906e