What Is the Structure of the Antitubercular Natural Product Eucapsitrione?

Glenn A. Pullella, Duncan A. Wild, Gareth L. Nealon, Mikhail Elyashberg, Matthew J. Piggott

Research output: Contribution to journalArticle

4 Citations (Scopus)

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 languageEnglish
Pages (from-to)7287-7299
Number of pages13
JournalJournal of Organic Chemistry
Volume82
Issue number14
DOIs
Publication statusPublished - 21 Jul 2017

Fingerprint

Biological Products
Cyclization
eucapsitrione
anthracene

Cite this

@article{c92df36bc2b54e708c90e7210529c49c,
title = "What Is the Structure of the Antitubercular Natural Product Eucapsitrione?",
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.",
author = "Pullella, {Glenn A.} and Wild, {Duncan A.} and Nealon, {Gareth L.} and Mikhail Elyashberg and Piggott, {Matthew J.}",
year = "2017",
month = "7",
day = "21",
doi = "10.1021/acs.joc.7b00863",
language = "English",
volume = "82",
pages = "7287--7299",
journal = "The Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "14",

}

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 journalArticle

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 -