1.
Org Lett
; 24(32): 6043-6048, 2022 08 19.
Artículo
en Inglés
| MEDLINE
| ID: mdl-35943240
RESUMEN
Melicoptelines, natural cyclopeptides containing a 3a-hydroxy hexahydropyrrolo[2,3-b]indole (HPI) moiety, exhibit anti-influenza activity. Herein, we report the first total synthesis of melicoptelines C-E (1-3, respectively). The core 3a-hydroxy HPIs were synthesized in a diastereoselective manner from l-tryptophan using dimethyldioxirane-mediated oxidation. Subsequently, sequential peptide couplings and cyclization completed the synthesis of melicoptelines C-E and unnatural melicopteline 4. The synthesized melicoptelines were evaluated for their anti-influenza activity, and melicopteline E showed the most potent inhibition of cytopathic effects.