The strong base-induced cycloaddition of 4-methoxy-5-methylpyrano[4,3-b]indole-1,3(4H,5H)-dione (3a) to 2-chloro-6-oxo-5,6,7,8-tetrahydro-1,4-naphthoquinone ethylene acetal (4) constitutes a regiospecific and convenient route to the D-ring indole analogue (2) of daunomycin.
Y. Tamura, M. Kirihara, M. Sasho, S. Akai, J. Sekihachi, R. Okunaka and Y. Kita, J. Chem. Soc., Chem. Commun., 1987, 1474 DOI: 10.1039/C39870001474
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