Synthesis of lysiformine, a marine-derived 3-hydroxypyridine alkaloid

A synthesis of the bisindole alkaloid lysiformine is reported. The heterocyclic skeleton of the natural product was assembled from a kojic acid-derived pyridine using iterative Suzuki coupling and reductive alkylation reactions. The NMR spectroscopic data of the synthetic sample was in excellent agreement to the natural product, confirming that lysiformine is a rare example of a marine natural product harbouring a 3-hydroxypyridine.

Automated summary

The synthesis of lysiformine, a bisindole alkaloid, was described. The heterocyclic framework of the natural product was assembled using iterative Suzuki coupling and reductive alkylation reactions starting from a pyridine derived from kojic acid. NMR spectroscopic analysis confirmed that the synthetic sample matched well with the natural product, highlighting the rarity of a marine natural product containing a 3-hydroxypyridine.