Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 7287-7299 |
| Number of pages | 13 |
| Journal | Journal of Organic Chemistry |
| Volume | 82 |
| Issue number | 14 |
| DOIs | |
| Publication status | Published - 21 Jul 2017 |
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What Is the Structure of the Antitubercular Natural Product Eucapsitrione? / Pullella, Glenn A.; Wild, Duncan A.; Nealon, Gareth L.; Elyashberg, Mikhail; Piggott, Matthew J.
In: Journal of Organic Chemistry, Vol. 82, No. 14, 21.07.2017, p. 7287-7299.Research output: Contribution to journal › Article
TY - JOUR
T1 - What Is the Structure of the Antitubercular Natural Product Eucapsitrione?
AU - Pullella, Glenn A.
AU - Wild, Duncan A.
AU - Nealon, Gareth L.
AU - Elyashberg, Mikhail
AU - Piggott, Matthew J.
PY - 2017/7/21
Y1 - 2017/7/21
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85025171609&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.7b00863
DO - 10.1021/acs.joc.7b00863
M3 - Article
VL - 82
SP - 7287
EP - 7299
JO - The Journal of Organic Chemistry
JF - The Journal of Organic Chemistry
SN - 0022-3263
IS - 14
ER -