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-Acyl­iminium Chemistry

Dedicated to the memory of our colleague, Professor Jean Morel, deceased on December 12, 2012 in Le Havre, France.

Abstract

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.

Key words

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

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