Rate-accelerating effect by the neighboring-group participation of protecting groups in the dehydrative cyclization of 1,3,5-triketones.
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.
Sakakura
Akira
A
Graduate School of Engineering, Nagoya University, Chikusa, Nagoya, Japan.
Watanabe
Hitoshi
H
Ishihara
Kazuaki
K
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
D001688:Biological Products; D007659:Ketones; D011753:Pyrones