title: Rate-accelerating effect by the neighboring-group participation of protecting groups in the dehydrative cyclization of 1,3,5-triketones.
abstract: Neighboring-group participation of an acyl protecting group efficiently promotes the Brønsted acid-catalyzed dehydrative cyclization of 1,3,5-triketones to gamma-pyrones, whereas a bulky silyloxy group in the beta-position retards the cyclization. This reaction provides an efficient synthetic route for a common intermediate for the synthesis of gamma-pyrone-containing bioactive natural products.
authors.affiliation: Graduate School of Engineering, Nagoya University, Chikusa, Nagoya, Japan.
authors.forename: Akira
authors.initials: A
authors.lastname: Sakakura
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Watanabe
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Ishihara
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis; D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D007659:Ketones; D011753:Pyrones