Lagunamides

The lagunamides have been isolated from lyngbya majus­cule, a sponge found in the southern lagoon of Pulau Hantu Besar in Singapore. They show high cytotoxicity towards a panel of tumor cell lines in a nanomolar range and also interesting anti malaria activity.

  • A. Tripathi, J. Puddick, M. R. Prinsep, P. P. F. Lee, L. T. Tan, J. Nat. Prod. 2010, 73, 1810–1814.
 

Matteson homologation was found to be an excellent tool for the synthesis of the polyketide fragment of lagunamide A. Starting from a chiral boronic ester a central building block containing all stereogenic centers of the polyketide chain was synthesized via six iterative Matteson homologation steps.

  • J. Gorges, U. Kazmaier, "Matteson Homologation-based Total Synthesis of Lagunamide A", Org. Lett. 2018, 20, 2033−2036.