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 | Zendy

Benoît Bolte | Zendy; Christopher S. Bryan | Zendy; Phillip P. Sharp | Zendy; Soheil Sayyahi | Zendy; Charly Rihouey | Zendy; Amy Kendrick | Zendy; Ping Lan | Zendy; Martin G. Banwell | Zendy; Colin J. Jackson | Zendy; Nicholas J Fraser | Zendy; Anthony C. Willis | Zendy; Jas S. Ward | Zendy

Open Access

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

Author(s) -

Benoît 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

Publication year - 2019

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.9b02725

Subject(s) - chemistry , palladium , quinolone , ullmann reaction , combinatorial chemistry , catalysis , coupling (piping) , coupling reaction , stereochemistry , medicinal chemistry , organic chemistry , mechanical engineering , biochemistry , engineering , antibiotics

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.

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