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Homoarcyriaflavin:  Synthesis of Ring-Expanded Arcyriaflavin Analogues

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journal contribution
posted on 06.10.1999, 00:00 by Siavosh Mahboobi, Thomas Burgemeister, Stefan Dove, Sabine Kuhr, Alfred Popp
The construction of the ring-expanded carbazole system, forming arcyriaflavin homologues, is efficiently accomplished by the reaction of 2,2‘-bridged bis-indoles with 3,4-dibromo-2,5-dihydro-1H-2,5-pyrroledione derivatives under Grignard conditions. A ring size of up to nine members in the central ring is achievable. Substitutions either at the indole system or at the imide-N are also possible. The conformation of homoarcyriaflavins as a cross-link between the rigid arcyriaflavins and the flexible arcyriarubins was investigated by NMR, X-ray, and semiempiric quantum chemical calculation methods.