Regioselective Nucleophilic Aromatic Substitution of Benzoic][2,7]naphthyridines

摘要

Over the past 25 years a number of biologically active natural products containing a benzo[c][2,7]naphthyridine subunit 1 have been reported. Invariably, these natural products are C-4 and C-5 substituted, usually in the form of an additional fused ring system, as seen in ascididemine 2. It was envisioned that these natural products could be synthesized via two nucleophilic aromatic substitutions of 1, at C-4 and C-5, accomplished through a series of sequential nucleophilic addition/dehydrogenation reactions utilizing appropriate dianion synthons such as 3.