2. Academic Validation
  3. Potassium Acetate-Catalyzed Double Decarboxylative Transannulation To Access Highly Functionalized Pyrroles

Potassium Acetate-Catalyzed Double Decarboxylative Transannulation To Access Highly Functionalized Pyrroles

  • Org Lett. 2020 Dec 18;22(24):9585-9590. doi: 10.1021/acs.orglett.0c03621.
Jun-Kuan Li 1 2,  Biying Zhou 3,  Yu-Chen Tian 1 2,  Chunman Jia 4,  Xiao-Song Xue 3,  Fa-Guang Zhang 1 2,  Jun-An Ma 1 2 3
Affiliations

Affiliations

  • 1 Department of Chemistry, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Frontiers Science Center for Synthetic Biology (Ministry of Education), and Tianjin Collaborative Innovation Centre of Chemical Science & Engineering, Tianjin University, Tianjin 300072, People's Republic of China.
  • 2 Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou 350207, People's Republic of China.
  • 3 State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
  • 4 Hainan Provincial Key Lab of Fine Chemistry, Hainan University, Haikou, Hainan 570228, People's Republic of China.
PMID: 33259210 DOI: 10.1021/acs.orglett.0c03621
Abstract

The development of new synthetic strategies for the efficient construction of versatile pyrrole pharmacores, especially in an operationally simple and environmentally benign fashion, still remains a momentous yet challenging goal. Here, we report a KOAc-catalyzed double decarboxylative transannulation between readily accessible oxazolones and isoxazolidinediones. This transformation represents a new way for skeletal remodeling by utilizing CO2 moiety as traceless activating and directing groups in both reaction partners. The synthetic value is evidenced by the rapid preparation of a broad spectrum of highly functionalized 3-carbamoyl-4-aryl pyrroles in good to excellent yields with exclusive regio-control, including the important Atorvastatin core.

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