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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 S; Sharp, Phillip P; Sayyahi, Soheil; Rihouey, Charly; Kendrick, Amy; Lan, Ping; Banwell, Martin G; Jackson, Colin J; Fraser, Nicholas J; Willis, Anthony C; Ward, Jas S.
Afiliação
  • Bolte B; Research School of Chemistry, Institute of Advanced Studies , The Australian National University , Canberra , ACT 2601 , Australia.
  • Bryan CS; Research School of Chemistry, Institute of Advanced Studies , The Australian National University , Canberra , ACT 2601 , Australia.
  • Sharp PP; Research School of Chemistry, Institute of Advanced Studies , The Australian National University , Canberra , ACT 2601 , Australia.
  • Sayyahi S; Research School of Chemistry, Institute of Advanced Studies , The Australian National University , Canberra , ACT 2601 , Australia.
  • Rihouey C; Research School of Chemistry, Institute of Advanced Studies , The Australian National University , Canberra , ACT 2601 , Australia.
  • Kendrick A; Research School of Chemistry, Institute of Advanced Studies , The Australian National University , Canberra , ACT 2601 , Australia.
  • Lan P; Institute for Advanced and Applied Chemical Synthesis , Jinan University , Guangzhou 510632 , China.
  • Banwell MG; Research School of Chemistry, Institute of Advanced Studies , The Australian National University , Canberra , ACT 2601 , Australia.
  • Jackson CJ; Institute for Advanced and Applied Chemical Synthesis , Jinan University , Guangzhou 510632 , China.
  • Fraser NJ; Research School of Chemistry, Institute of Advanced Studies , The Australian National University , Canberra , ACT 2601 , Australia.
  • Willis AC; Research School of Chemistry, Institute of Advanced Studies , The Australian National University , Canberra , ACT 2601 , Australia.
  • Ward JS; Research School of Chemistry, Institute of Advanced Studies , The Australian National University , Canberra , ACT 2601 , Australia.
J Org Chem ; 85(2): 650-663, 2020 01 17.
Article em En | MEDLINE | ID: mdl-31742404
ABSTRACT
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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Texto completo: 1 Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2020 Tipo de documento: Article País de afiliação: Austrália
Texto completo
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XML
PubMed Links
Buscar no Google

Texto completo: 1 Base de dados: MEDLINE Idioma: En Revista: J Org Chem Ano de publicação: 2020 Tipo de documento: Article País de afiliação: Austrália