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

Research output: Contribution to journalArticle

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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Urochordata
anthraquinones
Antimalarials
Biological Products
Anthraquinones
pathogens
synthesis
products
musculoskeletal system
toxicity
routes
Pathogens
Plasmodium falciparum
Skeleton
Toxicity
Cells
Derivatives
albopunctatone

Cite this

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
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. / Total synthesis of the antimalarial ascidian natural product albopunctatone. In: Organic Letters. 2019 ; Vol. 21, No. 14. pp. 5519-5523.
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Pullella, GA, Wdowiak, AP, Sykes, ML, Lucantoni, L, Sukhoverkov, KV, Zulfiqar, B, Sobolev, AN, West, NP, Mylne, JS, Avery, VM & Piggott, MJ 2019, 'Total synthesis of the antimalarial ascidian natural product albopunctatone' Organic Letters, vol. 21, no. 14, pp. 5519-5523. https://doi.org/10.1021/acs.orglett.9b01838

Total synthesis of the antimalarial ascidian natural product albopunctatone. / 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.

In: Organic Letters, Vol. 21, No. 14, 09.07.2019, p. 5519-5523.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Total synthesis of the antimalarial ascidian natural product albopunctatone

AU - Pullella, Glenn A

AU - Wdowiak, Adam P

AU - Sykes, Melissa L

AU - Lucantoni, Leonardo

AU - Sukhoverkov, Kirill V

AU - Zulfiqar, Bilal

AU - Sobolev, Alexandre N

AU - West, Nicholas P

AU - Mylne, Joshua S

AU - Avery, Vicky M

AU - Piggott, Matthew J

PY - 2019/7/9

Y1 - 2019/7/9

N2 - 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.

AB - 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.

U2 - 10.1021/acs.orglett.9b01838

DO - 10.1021/acs.orglett.9b01838

M3 - Article

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Pullella GA, Wdowiak AP, Sykes ML, Lucantoni L, Sukhoverkov KV, Zulfiqar B et al. Total synthesis of the antimalarial ascidian natural product albopunctatone. Organic Letters. 2019 Jul 9;21(14):5519-5523. https://doi.org/10.1021/acs.orglett.9b01838