A concise total synthesis of bruceolline E

doi:10.1016/j.tetlet.2011.10.023

Tetrahedron Letters

Volume 52, Issue 50, 14 December 2011, Pages 6772-6774

https://doi.org/10.1016/j.tetlet.2011.10.023 Get rights and content

Abstract

An efficient synthesis of bruceolline E was completed in three steps from the known ethyl indole-1-carboxylate (9d) in 60% overall yield, via a tandem acylation/Nazarov cyclization with 3,3-dimethyl acrylic acid followed by selenium dioxide oxidation to install the α-diketone functionality.

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Acknowledgments

Financial support from the UWI and the Government of Barbados is gratefully acknowledged.

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This article presents two types of phytochemical data obtained from Brucea javanica (L.) Merr. roots, a medicinal plant belonging to the Simaroubaceae family. The high-resolution LC–MS dataset comprised the chemical profile of dichloromethane extract, which was utilised to annotate 35 chemical constituents. For annotations, the measured spectral data were compared with the in-silico spectral data generated from 920 molecular structures previously reported in Simaroubaceae. Indole alkaloids, quassinoids, aliphatics and lignan were the chemical groups identified in the root extract. The second dataset provides NMR spectra (¹H, ¹³C, COSY, HMQC and HMBC) for the six indole alkaloids previously detected in LC–MS analysis and isolated through centrifugal partition chromatography. The chemical structures of all compounds were confirmed based on NMR data as bruceolline J (compound 7), canthin-6-one-N-oxide (compound 10), bruceolline E (compound 15), 5-methoxycanthin-6-one (compound 16), canthin-6-one (compound 20), and 1‑hydroxy-11-methoxycanthin-6-one (compound 22). This phytochemical data was generated to support an ongoing anti-cancer and anti-dengue study.
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A concise total synthesis of bruceolline E

Abstract

Graphical abstract

Section snippets

Acknowledgments

Helv. Chim. Acta

J. Heterocycl. Chem.

Helv. Chim. Acta

Org. Lett.

J. Chem. Soc., Perkin Trans. 1

J. Org. Chem.

J. Am. Chem. Soc.

J. Am. Chem. Soc.

J. Am. Chem. Soc.

J. Am. Chem. Soc.

Synth. Commun.

J. Org. Chem.

Neue Denkschrift. Allg. Schweiz. Nat. Ges.

Das Mikroskop

J. Phycol.

Photochem. Photobiol.

Experientia

Z. Naturforsch., C: Biosci.

J. Microbiol. Biotechnol.

Bioorg. Med. Chem. Lett.

Phytochemistry

Phytochemistry

Phytochemistry

Catal. Lett.

Org. Lett.

Synlett

Synthesis

J. Org. Chem.