Total synthesis of the antimalarial ascidian natural product albopunctatone

Glenn A Pullella, Adam P Wdowiak, Melissa L Sykes, Leonardo Lucantoni, Kirill V Sukhoverkov, Bilal Zulfiqar, Alexandre N Sobolev, Nicholas P West, Joshua S Mylne, Vicky M Avery, Matthew J Piggott

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Abstract

The first approaches to the 10'-anthronyl-2-anthraquinone skeleton have been devised, allowing two syntheses of the marine natural product albopunctatone. Both routes involve regioselective addition of a nucleophilic masked anthraquinone to a protected chrysazin derivative; the best affords albopunctatone in five steps and 35% overall yield. Albopunctatone exhibits potent inhibitory activity against Plasmodium falciparum and negligible toxicity to a range of other microbial pathogens and mammalian cells.

Original languageEnglish
Pages (from-to)5519-5523
Number of pages5
JournalOrganic Letters
Volume21
Issue number14
DOIs
Publication statusPublished - 9 Jul 2019

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Pullella, G. A., Wdowiak, A. P., Sykes, M. L., Lucantoni, L., Sukhoverkov, K. V., Zulfiqar, B., ... Piggott, M. J. (2019). Total synthesis of the antimalarial ascidian natural product albopunctatone. Organic Letters, 21(14), 5519-5523. https://doi.org/10.1021/acs.orglett.9b01838