Tetrahedron p. 3259 - 3268 (1986)
Update date:2022-08-05
Topics:
MacKenzie, A. Roderick
Moody, Christopher J.
Rees, Charles W.
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-benzyloxybenzaldehyde (5b) into methyl 6-acetamido-4-benzyloxyindole-2-carboxylate (7b) (74percent), followed by regioselective annulation of the third ring (55percent), and debenzylation and oxidation with benzoyl t-butyl nitroxide to give the tricyclic quinone triester (13) (methoxatin triester) (83percent).
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