181040-56-2Relevant academic research and scientific papers
Remote regiocontrol by a thioether group in Diels-Alder reactions of naphthazarin: Regioselective access to tetracyclic polyhydroxyquinones
Carreno, M. Carmen,Garcia Ruano, Jose L.,Urbano, Antonio
, p. 6136 - 6138 (2007/10/03)
The synthesis of tetracyclic polyhydroxyquinones 5a and 5b was achieved through a sequence involving two Diels-Alder reactions with 1-methoxy-1,3-cyclohexadiene: the first with 2-(p-tolylthio)naphthazarin and the second on the resulting tricyclic derivative previously transformed into a (p-tolylsulfinyl)naphthazarin. The success of this strategy stemmed from the efficient remote regiocontrol exerted by the thioether substituent in the first step.
