Synlett 2022; 33(17): 1770-1774
DOI: 10.1055/s-0042-1751356
letter

A Concise Total Synthesis of Steroid Scaffolds via a Palladium-Catalyzed Dearomatization Cyclization

Authors

  • Zhangwei Huang

    a   School of Perfume and Aroma Technology, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai, 201418, P. R. of China
  • Xianhua Pan

    a   School of Perfume and Aroma Technology, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai, 201418, P. R. of China
  • Lei Guo

    a   School of Perfume and Aroma Technology, Shanghai Institute of Technology, 100 Haiquan Road, Shanghai, 201418, P. R. of China
  • Wenjun Tang

    b   State Key Laboratory of Bio-Organic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai 200032, P. R. of China

We thank the talent research start-up fund of Shanghai Institute of Technology (YJ2022-14).


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Abstract

A concise total synthesis to generate synthetically challenging steroids scaffolds is reported utilizing palladium-catalyzed dearomatization cyclization for the key cyclization step, enabling the divergent synthesis of 6,6,6,5-tetracyclic steroids cores through both ligand and reaction condition control. We have started from the simple starting materials 2,4,6-trihydroxybenzoic acid and 2-methylcyclopentane-1,3-dione to selectively generate complex steroid scaffolds in a 12-step operation.

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Publikationsverlauf

Eingereicht: 01. Juni 2022

Angenommen nach Revision: 11. Juli 2022

Artikel online veröffentlicht:
19. August 2022

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