Total Synthesis of the Antimalarial Ascidian Natural Product Albopunctatone

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 albopunc...

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Bibliographic Details
Published in:Organic letters 2019-07, Vol.21 (14), p.5519-5523
Main Authors: Pullella, Glenn A, Wdowiak, Adam P, Sykes, Melissa L, Lucantoni, Leonardo, Sukhoverkov, Kirill V, Zulfiqar, Bilal, Sobolev, Alexandre N, West, Nicholas P, Mylne, Joshua S, Avery, Vicky M, Piggott, Matthew J
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b01838