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© Institut Pasteur
Cristaux de cellulase, enzyme purifiée de Clostridium thermocellum permettant la digestion de la cellulose. Image colorisée.
Publication : Synthesis

Antimycobacterial benzofuro[3,2-f]chromenes from a 5-bromochromen-6-ol

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Synthesis - 01 Jan 2007

Prado, S.; Toum, V.; Saint-Joanis, B.; Michel, S.; Koch, M.; Cole, S. T.; Tillequin, F.; Janin, Y. L.

Synthesis 2007, 1566-1570

In the course of our work on the synthesis of analogues of the specific antimycobacterial 3,3-dimethyl-3H-benzofuro[3,2- f]chromene, we prepared the previously unreported 5-bromo-2,2- dimethyl-2H-chromen-6-ol. We wish to report here an original syn- thetic scheme using this compound. The preparation of various 5- bromo-2,2-dimethyl-6-(aryloxy)-2H-chromenes was first investigated. This was followed by a palladium-catalysed cyclisation reaction, which takes place only in the presence of air, and leads to 3,3-dimethyl-3H-benzofuro[3,2-f]chromenes or 3,3-dimethyl-3H-4,7- dioxa-10-aza-benzo[c]fluorene. The antimycobacterial properties of these analogues have been investigated