Synthesis of substituted benzoates using a rhodium-mediated Hopf cyclization of 1, 3-dien-5-ynes accessed from 2-pyrones. (12th January 2023)

• Record Type: Journal Article
• Authors: Gardner, Kristen E.; Sarpong, Richmond
• Is Part Of: Tetrahedron letters. Volume 114(2023)
• Publication Date: 2023-01-12
• Subjects: 2-Pyrones -- Hopf cyclization -- 1, 3-Dien-5-ynes -- Cycloaromatization -- Benzoates; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2022.154272
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: The synthesis of substituted benzoates from 1, 3-dien-5-ynes that are readily accessed from 2-pyrones is described. Highlighted is a 2-pyrone remodeling strategy in which a 3-alkynyl-2-pyrone is selectively opened in a 1, 6-fashion using sodium cyanide to provide dienynes that upon treatment with sub-stoichiometric amounts of [Rh(CO)2 Cl]2 at elevated temperature furnish the desired benzoate.