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

Lahssen El Blidi; Aurélie Namoune; Alexandre Bridoux; Vijaykumar D. Nimbarte; Ata Martin Lawson; Sébastien Comesse; Adam Daïch

doi:10.1055/s-0034-1378811

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(22): 3583-3592
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

Lahssen El Blidi

^aLaboratoire de Chimie, URCOM, EA 3221, INC3M CNRS-FR 3038, UFR des Sciences et Techniques, Université du Havre, BP: 1123, 25 rue Philipe Lebon, 76063 Le Havre Cedex, France eMail: adam.daich@univ-lehavre.fr

^bChemical Engineering Department, College of Engineering, King Saud University, P.O. Box 800, Riyadh 11421, Kingdom of Saudi Arabia

,

Aurélie Namoune

^aLaboratoire de Chimie, URCOM, EA 3221, INC3M CNRS-FR 3038, UFR des Sciences et Techniques, Université du Havre, BP: 1123, 25 rue Philipe Lebon, 76063 Le Havre Cedex, France eMail: adam.daich@univ-lehavre.fr

,

Alexandre Bridoux

^aLaboratoire de Chimie, URCOM, EA 3221, INC3M CNRS-FR 3038, UFR des Sciences et Techniques, Université du Havre, BP: 1123, 25 rue Philipe Lebon, 76063 Le Havre Cedex, France eMail: adam.daich@univ-lehavre.fr

,

Vijaykumar D. Nimbarte

^aLaboratoire de Chimie, URCOM, EA 3221, INC3M CNRS-FR 3038, UFR des Sciences et Techniques, Université du Havre, BP: 1123, 25 rue Philipe Lebon, 76063 Le Havre Cedex, France eMail: adam.daich@univ-lehavre.fr

,

Ata Martin Lawson

^aLaboratoire de Chimie, URCOM, EA 3221, INC3M CNRS-FR 3038, UFR des Sciences et Techniques, Université du Havre, BP: 1123, 25 rue Philipe Lebon, 76063 Le Havre Cedex, France eMail: adam.daich@univ-lehavre.fr

,

Sébastien Comesse

^aLaboratoire de Chimie, URCOM, EA 3221, INC3M CNRS-FR 3038, UFR des Sciences et Techniques, Université du Havre, BP: 1123, 25 rue Philipe Lebon, 76063 Le Havre Cedex, France eMail: adam.daich@univ-lehavre.fr

,

Adam Daïch*

^aLaboratoire de Chimie, URCOM, EA 3221, INC3M CNRS-FR 3038, UFR des Sciences et Techniques, Université du Havre, BP: 1123, 25 rue Philipe Lebon, 76063 Le Havre Cedex, France eMail: adam.daich@univ-lehavre.fr

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Abstract

Alle Artikel dieser Rubrik

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)

Volltext

Referenzen

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Zusatzmaterial

Supporting Information

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

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