Palladium-catalyzed post-Ugi arylative dearomatization/Michael addition cascade towards plicamine analogues

A palladium-catalyzed intramolecular cyclization of Ugi-adductsviaa cascade dearomatization/aza-Michael addition process has been developed. Diverse plicamine analogues are constructed in a rapid, highly efficient and step-economical manner, through the combination of an Ugi-4CR and a palladium-catalyzed dearomatization. The synthetic utility of this approach is illustrated by further functional group transformations. © The Royal Society of Chemistry 2021.

Authors
Liu C.1 , Zhao R.1 , Song L.2 , Li Z.1 , Tian G.1 , He Y.1 , Van Meervelt L. , Peshkov V.A.4, 5 , Van Der Eycken E.V.
Journal
Organic and Biomolecular Chemistry
Publisher
Royal Society of Chemistry
Number of issue
44
Language
English
Pages
9752-9757
Status
Published
Link
External link
DOI
10.1039/d1ob01805a
Volume
19
Year
2021
Organizations
  • 1 Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, KU Leuven Celestijnenlaan 200F, Leuven, 3001, Belgium
  • 2 Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, Jiangsu Key Lab of Biomass-Based Green Fuels and Chemicals, International Innovation Center for Forest Chemicals and Materials, College of Chemical Engineering, Nanjing Forestry University, Jiangsu, Nanjing, 210037, China
  • 3 Biomolecular Architecture, Department of Chemistry, KU Leuven Celestijnenlaan 200F, Leuven, 3001, Belgium
  • 4 College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, China
  • 5 Department of Chemistry, School of Sciences and Humanities, Nazarbayev University, 53 Kabanbay Batyr Ave, Nur-Sultan, 010000, Kazakhstan
  • 6 Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya Street 6, Moscow, 117198, Russian Federation
Keywords
Catalysis; Cyclization; Palladium; Aza-Michael addition; Dearomatization; Functional group transformations; Intramolecular cyclizations; Michael additions; Palladium-catalyzed; Synthetic utility; Aromatization
Date of creation
16.12.2021
Date of change
16.12.2021
Short link
https://repository.rudn.ru/en/records/article/record/76485/
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