Total Synthesis of the Antimalarial Ascidian Natural Product Albopunctatone

Org Lett. 2019 Jul 19;21(14):5519-5523. doi: 10.1021/acs.orglett.9b01838. Epub 2019 Jul 9.


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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anthraquinones / chemical synthesis*
  • Anthraquinones / chemistry*
  • Anthraquinones / pharmacology
  • Antimalarials / chemical synthesis*
  • Antimalarials / chemistry*
  • Antimalarials / pharmacology
  • Cell Line
  • Chemistry Techniques, Synthetic
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Plasmodium falciparum / drug effects
  • Urochordata / chemistry*


  • Anthraquinones
  • Antimalarials
  • albopunctatone