Photocatalyzed de novo synthesis of fused tetracyclic skeletons via stepwise formal [3 + 2]/[4 or 5 + 2] cycloadditions

Abstract

We successfully developed an unprecedented visible light-promoted synthesis route to fused tetracyclic skeletons with rich sp3 carbons through stepwise radical cycloadditions and further cyclization of the final radical intermediates with adjacent aromatic rings. This convenient and sustainable protocol features mild reaction conditions, excellent H2O and air tolerance, good functional group compatibility and wide substrate adaptability. Moreover, based on direct excitation, radical-trapping, radical clock, and EPR experiments, a possible stepwise formal [3 + 2]/[4 or 5 + 2] cycloaddition process was proposed.

Graphical abstract: Photocatalyzed de novo synthesis of fused tetracyclic skeletons via stepwise formal [3 + 2]/[4 or 5 + 2] cycloadditions

Supplementary files

Article information

Article type
Research Article
Submitted
16 Sep 2024
Accepted
28 Sep 2024
First published
07 Oct 2024

Org. Chem. Front., 2024, Advance Article

Photocatalyzed de novo synthesis of fused tetracyclic skeletons via stepwise formal [3 + 2]/[4 or 5 + 2] cycloadditions

W. Guan, J. Hang, G. Liu, Y. Qiao, C. Yuan, L. Liao, X. Fan, Z. Fang, C. Liu and K. Guo, Org. Chem. Front., 2024, Advance Article , DOI: 10.1039/D4QO01729C

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