title: Development of a Brønsted acid-promoted arene-ynamide cyclization toward the total syntheses of marinoquinolines A and C and aplidiopsamine A.
abstract: A Brønsted acid-promoted arene-ynamide cyclization has been developed to construct the 3H-pyrrolo[2,3-c]quinolines. This reaction consists of the generation of a highly reactive keteniminium intermediate from arene-ynamide activated by a Brønsted acid and electrophilic aromatic substitution reaction to give arene-fused quinolines in high yields. This methodology enabled facile access to marinoquinolines A and C and aplidiopsamine A.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University , Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
authors.forename: Yousuke
authors.initials: Y
authors.lastname: Yamaoka
authors.forename: Takahiro
authors.initials: T
authors.lastname: Yoshida
authors.forename: Makiko
authors.initials: M
authors.lastname: Shinozaki
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Yamada
authors.forename: Kiyosei
authors.initials: K
authors.lastname: Takasu
mesh_terms: D000143:Acids / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000143:Acids; D011758:Pyrroles; D011804:Quinolines; C555847:aplidiopsamine A; C558971:marinoquinoline A; C000600029:marinoquinoline C