Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

What Is the Structure of the Antitubercular Natural Product Eucapsitrione?

What Is the Structure of the Antitubercular Natural Product Eucapsitrione?
Matthew J. Piggott, Gareth L. Nealon, Duncan A. Wild, Mikhail Elyashberg, Glenn A. Pullella
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00863

DOI: 10.1021/acs.joc.7b00863

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