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

2000; Royal Society of Chemistry; Issue: 16 Linguagem: Inglês

10.1039/b004029k

2050-8263

Jan Bergman, Eva Koch, Benjamin Pelcman,

Bioactive natural compounds

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