Internal amide-triggered cycloaromatization of maduropeptin-like nine-membered enediyne.
In the Masamune-Bergman cyclization of a nine-membered non-conjugated enediyne with an internal, maduropeptin-like nucleophile, the exocyclic alkene migrated to form the nine-membered conjugated enediyne, triggered by the intramolecular addition of the amide group; final aromatized products showed up to 85% yield.
Norizuki
Yutaro
Y
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, Japan.
Komano
Kazuo
K
Sato
Itaru
I
Hirama
Masahiro
M
D000577:Amides / Q000737:chemistry*; D003500:Cyclization; D053281:Enediynes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000577:Amides; D053281:Enediynes; D006571:Heterocyclic Compounds; C509891:maduropeptin enediyne