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Synthesis 2022; 54(24): 5337-5359
DOI: 10.1055/a-1918-4338
DOI: 10.1055/a-1918-4338
review
Metal-Catalyzed C–H Bond Oxidation in the Total Synthesis of Natural and Unnatural Products
We are grateful to São Paulo Research Foundation (FAPESP) for the financial support for this work (grant 2018/04837-6) and fellowships to V. C. S. Santana and M. C. V. Fernandes (grants 2019/27528-1 and 2021/07167-4). We also thank CNPq, CAPES, and FAEPEX-UNICAMP (2575/21).
Abstract
C–H bond oxidation is a powerful means for oxygen incorporation in organic molecules. Its use results in fast structural diversification and in a new way of thinking about retrosynthetic disconnections. In this review, we present the application of five metal-catalyzed methodologies for C(sp 3)–H oxidation in the total synthesis of natural and unnatural products, covering the period of 2004–2022.
1 Introduction
2 Copper-Mediated Hydroxylation of Methylenes β to Imines
3 Palladium Acetoxylation of Methyl Groups β to Oximes
4 Palladium-Mediated Allylic C–H Bond Oxidation of Terminal Olefins
5 Iron- and Manganese-Mediated Aliphatic Oxidation
6 Miscellaneous
7 Conclusion
Publikationsverlauf
Eingereicht: 30. April 2022
Angenommen nach Revision: 04. August 2022
Accepted Manuscript online:
04. August 2022
Artikel online veröffentlicht:
06. Oktober 2022
© 2022. Thieme. All rights reserved
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For recent reviews of C–H functionalization in total synthesis, see:
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For other total syntheses of paspaline, see:
For other total syntheses of hippolachnin A, see:
For other total synthesis of (–)-mitrephorone A, see: