Remote Regiocontrol by a Thioether Group in Diels−Alder Reactions of Naphthazarin: Regioselective Access to Tetracyclic Polyhydroxyquinones
- 1 January 1996
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 61 (18) , 6136-6138
- https://doi.org/10.1021/jo960855n
Abstract
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.Keywords
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