3-Alkylpyridine alkaloids (3-APAs) are a class of alkaloids containing at least one pyridinium or tetrahydropyridine moiety most commonly connected at the 1- and/or 3-position to an alkyl chain known to have promising biological activity. A total of five different classes have been isolated from the arctic sponge <i>Haliclona viscosa</i>. However, their limited bioavailability has significantly hampered detailed investigations of their bioactivity. Further, synthesis of an intermediate common to all five classes requires harsh conditions and the use of protecting groups. In this work, we developed a concise 2-step route enabling us to synthesize a total of 2 natural and 7 synthetic 3-APAs belonging to the haliclocyclins class. Their bioactivity was briefly investigated, and they displayed modest antibiotic activity against several Gram-positive bacterial strains.

An efficient synthesis of 3-alkylpyridine alkaloids enables their biological evaluation

ACS Fall 2021

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