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What Is the Structure of the Antitubercular Natural Product Eucapsitrione?

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journal contribution
posted on 21.06.2017, 00:00 by Glenn A. Pullella, Duncan A. Wild, Gareth L. Nealon, Mikhail Elyashberg, Matthew J. Piggott
1,5,7-Trihydroxy-6H-indeno­[1,2-b]­anthracene-6,11,13-trione (1), proposed to be the antitubercular natural product eucapsitrione, has been synthesized in 43% overall yield and six steps, including a key Suzuki–Miyaura biaryl coupling and a directed remote metalation (DReM)-initiated cyclization. The physical and spectroscopic properties of 1 do not match the data reported for the natural product. At this time there is insufficient information available to enable a structure reassignment. During the optimization of the Suzuki–Miyaura coupling, an unprecedented biaryl coupling ortho to the borono group was observed. The scope of this unusual reaction has been investigated.