Triple-dearomative photocycloaddition: a strategy to construct caged molecular frameworks
Files
Accepted manuscript
Date
2024-05-15
Authors
Ji, Kaijie
Parthiban, Jayachandran
Jockusch, Steffen
Sivaguru, Jayaraman
Porco, John A.
Version
Accepted manuscript
OA Version
Citation
K. Ji, J. Parthiban, S. Jockusch, J. Sivaguru, J.A. Porco. 2024. "Triple-Dearomative Photocycloaddition: A Strategy to Construct Caged Molecular Frameworks." Journal of the American Chemical Society, Volume 146, Issue 19, pp.13445-13454. https://doi.org/10.1021/jacs.4c02674
Abstract
An unprecedented caged 2H-benzo-dioxo-pentacycloundecane framework was serendipitously obtained in a single transformation via triple-dearomative photocycloaddition of chromone esters with furans. This caged structure was generated as part of an effort to access a tricyclic, oxygen-bridged intermediate enroute to the dihydroxanthone natural product nidulalin A. Reaction scope and limitations were thoroughly investigated, revealing the ability to access a multitude of synthetically challenging caged scaffolds in a two-step sequence. Photophysical studies provided key mechanistic insights on the process for formation of the novel caged scaffold.