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Palladium-Catalyzed C-H Olefination for Nucleic Acid Production.

Ruoqian Xie1, Yunxi Han1, Wenhao Luo1

  • 1Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai, People's Republic of China.

Current Protocols
|July 27, 2023
PubMed
Summary

This study introduces a palladium-catalyzed direct C-H olefination method for unprotected uridine and its analogues. This efficient process enables the introduction of alkenyl groups at the uracil C5 position without pre-functionalization.

Keywords:
C-H olefinationPd-catalyzedlate-stage functionalizationnucleoside analoguesuridine

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Catalysis

Background:

  • Uracil derivatives are crucial nucleosides in biological systems and pharmaceuticals.
  • Direct functionalization of nucleosides offers a more efficient synthetic route compared to traditional methods.
  • Palladium-catalyzed C-H activation has emerged as a powerful tool in organic synthesis.

Purpose of the Study:

  • To develop a direct C-H olefination protocol for unprotected uridine and its analogues.
  • To introduce alkenyl groups at the C5 position of the uracil ring efficiently.
  • To synthesize novel C5-alkenylated uridine analogues with potential pharmaceutical applications.

Main Methods:

  • Palladium-catalyzed direct C-H activation and olefination.
  • Utilizing unprotected uridine, 2'-deoxyuridine, uridine monophosphate, and analogues.
  • Employing methyl acrylate and styrene as alkenylating agents.

Main Results:

  • Successful C5-alkenylation of uridine and 2'-deoxyuridine without pre-functionalization.
  • Synthesis of various C5-alkenylated uridine analogues with exposed hydroxyl groups.
  • Demonstration of an atom-economical and environmentally friendly synthetic approach.

Conclusions:

  • The developed protocol offers an efficient and green method for C5-functionalization of uracil nucleosides.
  • The synthesized analogues represent potential candidates for drug discovery.
  • Direct C-H olefination provides a valuable strategy for accessing diverse nucleoside derivatives.