Synthetic anthracyclines: Total synthesis of D-ring pyridine and pyrazine analogues of 11-deoxydaunomycin.

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Abstract
Treatment of sodium salts generated from tetrahydrohomophthalic anhydrides (6a, b) with 5, 8-dihydro-5, 8-dioxoquinoline (9) gave cycloadducts (7 and 8), regioselectively. These adducts were converted to the D-ring pyridine analogue (21) of 11-deoxydaunomycin. The D-ring pyrazine analogue (27) of 11-deoxydaunomycin was also prepared by a similar method.

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