Shortest Enantioselective Total Syntheses of (+)-Isolaurepinnacin and (+)-Neoisoprelaurefucin

A short cut to making medicinal seaweed-derived compounds

1 November 2022

Two compounds derived from red seaweeds that are promising for medical use have been synthesised in the lab using the shortest path to date.

Red seaweeds of the genus Laurencia produce compounds belonging to the lauroxane family, which exhibit a wide range of biological properties such as being effective against tumours and epilepsy.

Now, a team led by a researcher from University of La Laguna has demonstrated a way to synthesis two lauroxanes that involves the shortest pathway found so far.

This demonstration builds on previous work they had done on a highly efficient reaction known as Prins–Peterson cyclization, which was the pivotal step in the present synthesis. Using this reaction allowed the researchers to reduce the number of steps in the synthesis.

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References

1. Organic Letters 24, 5271−5275 (2022). doi: 10.1021/acs.orglett.2c01769