jo981926g_si_001.pdf (234.68 kB)
Homoarcyriaflavin: Synthesis of Ring-Expanded Arcyriaflavin Analogues†
journal contribution
posted on 1999-10-06, 00:00 authored by Siavosh Mahboobi, Thomas Burgemeister, Stefan Dove, Sabine Kuhr, Alfred PoppThe 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.