Abstract
A short total synthesis of the bacterial coenzyme methoxatin (1) (4,5-dihydro-4, 5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid) is described. The route involves the two step conversion of 4-acetamido-2-benzy1oxybenzaldehyde (5b) into methyl 6-acctamido-4-benzyloxyindole-2-carboxylate (7b) (74%), followed by regioselective annulation of the third ring (55%),and debenzylation and oxidation with benzoyl t-butyl nitroxide to give the tricyclic quinone triester (13) (methoxatin triester) (83%).
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