Total Synthesis of Aleutianamine

19 September 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


ABSTRACT: Aleutianamine is a recently isolated pyrroloiminoquinone natural product that displays potent and selective biological activity toward human pancreatic cancer cells with an IC50 = 25 nM against PANC-1, making it a potential candi-date for therapeutic development. We report a synthetic approach to aleutianamine wherein the unique [3.3.1] ring system and tertiary sulfide of this alkaloid were constructed via a novel palladium-catalyzed dearomative thiophene functionalization. Other highlights of the synthesis include a palladium-catalyzed decarboxylative pinacol-type rearrangement of an allylic car-bonate to install a ketone and a late-stage oxidative amination. This concise and convergent strategy will enable access to analogues of aleutianamine and further investigation of the biological activity of this unique natural product.


Total Synthesis
Palladium Catalysis
Natural Product Synthesis

Supplementary materials

Supporting Information
Experimental details and spectral data


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Comment number 1, This comment has been removed by the moderator.: Sep 19, 2023, 19:29
This comment has been removed by the moderator.