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
dataset
posted 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. WardCompounds 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.
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marinoquinoline familyacetylcholinesteraseCyclizationTotal SynthesesPalladium-CatalyzedAplidiopsaminemembercongener 2palladium-catalyzed Ullmann cross-couplingPathwayquinolone-Containing Alkaloids MarinoquinolinesAChEinhibitorcombinationCross-Couplingreductive cyclization processesmarine alkaloid aplidiopsamineC 3-arylated pyrrolePyrroloCompoundsingle-crystal X-ray analyses
