5,6-Dihydrobenzo[a]naphthacenequinone has been constructed by Diels-Alder reaction of an outer-ring diene with a naphthoquinone regioselectively. Similarly, the 14-hydroxy-5,6-dihydrobenzo[a]naphthacenequinone (13) has also been synthesized via the reaction of vinylketene acetal (11) with naphthoquinone.
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Hirosawa et al. (1997) studied this question.
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