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
Organic Letters
Number of issue
21
Language
English
Pages
8441-8445
Status
Published
Link
External link
DOI
10.1021/ACS.ORGLETT.0C03062
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
Cite
ГОСТ MLA RIS BibTex
Share

Other records

NOVEL COPPER-CONTAINING CYTOTOXIC AGENTS BASED ON 2-THIOXOIMIDAZOLONES

Article
Krasnovskaya O.O., Guk D.A., Naumov A.E., Nikitina V.N., Semkina A.S., Vlasova K.Y., Pokrovsky V., Ryabaya O.O., Karshieva S.S., Skvortsov D.A., Zhirkina I.V., Shafikov R.R., Gorelkin P.V., Vaneev A.N., Erofeev A.S., Mazur D.M., Tafeenko V.A., Pergushov V.I., Melnikov M.Y., Soldatov M.A., Shapovalov V.V., Soldatov A.V., Akasov R.A., Gerasimov V.M., Sakharov D.A., Moiseeva A.A., Zyk N.V., Beloglazkina E.K., Majouga A.G.
Journal of Medicinal Chemistry. American Chemical Society. Vol. 63. 2020. P. 13031-13063