Synthesis of pyrone-annulated 2-oxabicyclo[3.3.1]nonanes by palladium-catalyzed cyclization of 4-hydroxy-2-pyrones with allylic bisacetates. Issue 49 (5th December 2019)

• Record Type: Journal Article
• Authors: Yoshida, Masahiro; Shibata, Miki; Mukae, Saaya; Kinoshita, Kouki; Matsumoto, Kenji; Hirokane, Tsukasa
• Is Part Of: Tetrahedron letters. Volume 60:Issue 49(2019)
• Publication Date: 2019-12-05
• Subjects: Palladium -- Cyclization -- π-Allylpalladium -- Pyrones; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.151262
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A Pd-catalyzed reaction of 4-hydroxy-2-pyrones with 1, 4-diacetoxy-2-cyclohexene. A pyrone-annulated 2-oxabicyclo[3.3.1]nonane scaffold has been constructed. Furo[3, 2- c ]pyranone was produced by decreasing the reaction temperature. Abstract: Cyclization of 4-hydroxy-2-pyrones with allylic bisacetates by a palladium catalyst is described. Pyrone-annulated 2-oxabicyclo[3.3.1]nonane derivatives were regioselectively produced from the reaction of 4-hydroxy-2-pyrones with 1, 4-diacetoxy-2-cyclohexene at high temperature. The reaction would proceed via a migration of the π-allylpalladium intermediate.