S. Hirosawa et al., A SYNTHETIC APPROACH TO BENANOMICIN-A .1. SYNTHESIS OF 5,6-DIHYDROBENZO[A]NAPHTHACENEQUINONE, Journal of antibiotics, 50(8), 1997, pp. 685-689
5,6-Dihydrobenzo[a]naphthacenequinone has been constructed by DIELS-AL
DER reaction of an outer-ring diene with a naphthoquinone regioselecti
vely. Similarly, the 14-hydroxy-5,6-dihydrobenzo[a]naphthacenequinone
(13) has also been synthesized via the reaction of vinylketene acetal
(11) with naphthoquinone.