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Synthesis 2015; 47(22): 3583-3592
DOI: 10.1055/s-0034-1378811
DOI: 10.1055/s-0034-1378811
paper
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
Further Information
Publication History
Received: 03 April 2015
Accepted after revision: 11 June 2015
Publication Date:
07 September 2015 (online)
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)Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1378811.
- Supporting Information
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For general reviews, see:
For reviews on the synthesis of natural and unnatural compounds using radical cyclization, see:
For 5-substitued isoquinolines except the halogenated derivatives, see:
The preparation of the brominated acid is inspired by the sequence used for the preparation of its chlorinated analogue according to reports by Dey et al. in 1970 and Kan et al. in 1964, respectively. This one brings in an isothiocyanate prepared from the commercially available 2-bromophenylacetic acid followed by its commitment in the Friedel–Crafts reaction to integrate the acid function on the ortho position of the benzene ring.
See recent examples: