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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.

A Synthehc Approach to Benanomicin A. 1. Synthesis of 5,6-Dihydrobenzo(a)naphthacenequinone.