Apratoxin

The apratoxins are a class of cyclodepsipeptides produced by cyano-bacteria. The first described member of this group, apratoxin A, was isolated by Moore and Paul et al. from the marine cyanobacterium Lyngbya majuscula in 2001. It showed potent cytotoxicity towards a range of tumor cell lines in the sub nanomolar range.

  • H. Luesch, W. Y. Yoshida, R. E. Moore, V. J. Paul and T. H. Corbett, J. Am. Chem. Soc. 2001, 123, 5418–5423.
  • Y. Liu, B. K. Law and H. Luesch, Mol. Pharmacol. 2009, 76, 91–104.
 

Apratoxin A and B, two members of an interesting class of marine cyclodepsipeptides are synthesized in a straightforward manner via Matteson homologation. Starting from a chiral boronic ester, the polyketide fragment of the apratoxins was obtained via five successive homologations steps. This approach is highly flexible and should allow modification also of this part of the natural products.

  • O. Andler, U. Kazmaier, "Total Synthesis of Apratoxin A and B using Matteson's Homologation Approach", Org. Biomol. Chem. 2021, 19, 4866–4870. DOI: 10.1039/d1ob00713k.