A Gold(I)-Catalyzed Hydroamination/Cycloisomerization Cascade: Concise Synthesis of (±)-seco-Antofine and (±)-Septicine

A concise and flexible procedure for the synthesis of highly functionalized N-heterocyclic 1,6-annulated 2-pyridones and 2,3-annulated 4-pyrimidinones has been elaborated through a gold-catalyzed tandem hydroamination/cycloisomerization cascade. This novel and highly efficient method allows the rapid construction of these diverse N-heterocyclic scaffolds starting from readily available building blocks, and shows a wide scope and good functional group tolerance. The total synthesis of (±)-seco-antofine and (±)-septicine were realized employing this strategy. © 2020 American Chemical Society.

Authors
Tian G.1 , Song L.1 , Li Z.1 , Robeyns K.2 , Van Meervelt L. , Van Der Eycken E.V.
Journal
Number of issue
21
Language
English
Pages
8441-8445
Status
Published
Volume
22
Year
2020
Organizations
  • 1 Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 2 IMCN, Molecules Solids and Reactivity Division (MOST), Université Catholique de Louvain, Place Pasteur 1, Louvain-la-Neuve, B-1348, Belgium
  • 3 Biomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 4 Peoples' Friendship University of Russia, RUDN University, 6 Miklukho-Maklaya Street, Moscow, 117198, Russian Federation
Date of creation
20.04.2021
Date of change
20.04.2021
Short link
https://repository.rudn.ru/en/records/article/record/72438/
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