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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

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
› Author AffiliationsWe 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.

Key words

total synthesis - steroids scaffolds - palladium catalysis - dearomatization cyclization - 6,6,6,5-tetracyclic steroids

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751356.
  • Supporting Information


Publication History

Received: 01 June 2022

Accepted after revision: 11 July 2022

Article published online:
19 August 2022

© 2022. Thieme. All rights reserved

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