title: Internal amide-triggered cycloaromatization of maduropeptin-like nine-membered enediyne.
abstract: 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.
authors.affiliation: Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, Japan.
authors.forename: Yutaro
authors.initials: Y
authors.lastname: Norizuki
authors.forename: Kazuo
authors.initials: K
authors.lastname: Komano
authors.forename: Itaru
authors.initials: I
authors.lastname: Sato
authors.forename: Masahiro
authors.initials: M
authors.lastname: Hirama
mesh_terms: D000577:Amides / Q000737:chemistry*; D003500:Cyclization; D053281:Enediynes / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000577:Amides; D053281:Enediynes; D006571:Heterocyclic Compounds; C509891:maduropeptin enediyne