4.5 Article

Expeditious Synthesis of the Topoisomerase I Inhibitors Isoindolo-[2,1-b]isoquinolin-7(5H)-one and the Alkaloid Rosettacin Based on Aryl Radical Cyclization of Enamide Generated by Using N-Acyl-iminium Chemistry

Journal

SYNTHESIS-STUTTGART
Volume 47, Issue 22, Pages 3583-3592

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1378811

Keywords

N-acyliminium; aromathecins; rosettacin; aryl radical cyclization; enamide; topoisomerase I (Topo1)

Funding

  1. French Ministry of Higher Education and Research

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A short and effective approach to the synthesis of the topoisomerase I inhibitor isoindolo[2,1-b] isoquinolin-7(5H)-one and the alkaloid rosettacin belonging to the aromathecin family is presented. The key step of this sequence, which resulted in the formation of a five-membered ring, was the aryl radical cyclization of enamides generated using N-acyliminium chemistry.

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