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Total Syntheses of the 3H-Pyrrolo[2,3-c]quinolone-Containing Alkaloids Marinoquinolines A-F, K, and Aplidiopsamine A Using a Palladium-Catalyzed Ullmann Cross-Coupling/Reductive Cyclization Pathway

Bolte, Benoit; Bryan, Christopher; Sharp, Phillip; Sayyahi, Soheil; Rihouey, Charly; Kendrick, Amy; Lan, Ping; Banwell, Martin; Jackson, Colin; Fraser, Nicholas; Willis, Anthony; Ward, Jas


Compounds 1-6 and 11 representing key members of the marinoquinoline family of natural products, together with the related marine alkaloid aplidiopsamine A (12), have been synthesized using various combinations of palladium-catalyzed Ullmann cross-coupling and reductive cyclization processes involving a C3-arylated pyrrole as the common intermediate. These natural products have been characterized by single-crystal X-ray analyses and evaluated as inhibitors of acetylcholinesterase (AChE) with...[Show more]

CollectionsANU Research Publications
Date published: 2019-11-19
Type: Journal article
Source: The Journal of organic chemistry
DOI: 10.1021/acs.joc.9b02725
Access Rights: Open Access


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