Coupling reactions of indole-3-acetic acid derivatives. Synthesis of arcyriaflavin A

The bisindolesuccinic acid methyl ester 10 was obtained by an iodine-promot ed coupling of the dianion 9. The diester was converted to the N-benzylimid e 12, which was oxidatively cyclized to the indolo[2,3-a]pyrrolo[3,4-c]carb azole 15. The diester 10 could be directly transformed to the known indoloc arbazole diester 27 via acid-induced intramolecular cyclization in TFA. The same methodology gave arcyriaflavin A 4 from the succinimide 18b.