jo9b02725_si_016.cif (61.79 kB)
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
datasetposted on 2019-12-17, 22:05 authored by Benoit Bolte, Christopher S. Bryan, Phillip P. Sharp, Soheil Sayyahi, Charly Rihouey, Amy Kendrick, Ping Lan, Martin G. Banwell, Colin J. Jackson, Nicholas J. Fraser, Anthony C. Willis, Jas S. Ward
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 congener 2 proving to be the most active.
marinoquinoline familyacetylcholinesteraseCyclizationTotal SynthesesPalladium-CatalyzedAplidiopsaminemembercongener 2palladium-catalyzed Ullmann cross-couplingPathwayquinolone-Containing Alkaloids MarinoquinolinesAChEinhibitorcombinationCross-Couplingreductive cyclization processesmarine alkaloid aplidiopsamineC 3-arylated pyrrolePyrroloCompoundsingle-crystal X-ray analyses