Synthesis of Morphinans through Anodic Aryl-Aryl Coupling.
Nina Vierengel1, Leander Geske1, Eisuke Sato1
1Department Chemie, Johannes Gutenberg University, Duesbergweg 10-14, 55128, Mainz, Germany.
Chemical Record (New York, N.Y.)
|May 6, 2021
Summary
Electrosynthesis offers a novel pathway for creating morphinan alkaloids, including morphine derivatives. This review details historical advancements in using anodic aryl-aryl couplings for morphinan synthesis.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- Morphinans, like morphine, are vital natural products with a long history of medicinal use.
- Modern research focuses on modifying the morphinan core to enhance therapeutic effects and minimize side effects.
- The complex structure of morphinans presents significant challenges for total synthesis.
Purpose of the Study:
- To review electrosynthetic strategies for constructing natural and semisynthetic morphinan alkaloids.
- To chronologically outline the historical development of anodic aryl-aryl couplings in morphinan framework assembly.
- To analyze the advantages and disadvantages of electrochemical methods in morphinan synthesis.
Main Methods:
- Focuses on electrosynthetic approaches, specifically anodic aryl-aryl couplings.
- Reviews historical progress in applying these electrochemical methods.
- Discusses the impact of various factors like substitution patterns, protecting groups, and reaction conditions.
Main Results:
- Highlights the successful application of electrosynthesis in building the morphinan core.
- Chronological review of key advancements in electrochemical morphinan synthesis.
- Analysis of how different reaction parameters influence the efficiency and outcome of electrosynthesis.
Conclusions:
- Electrosynthesis provides a powerful and versatile tool for accessing morphinan alkaloids.
- Anodic aryl-aryl couplings are a key electrochemical strategy for morphinan framework construction.
- Understanding the influence of reaction conditions is crucial for optimizing electrosynthetic routes to morphinans.
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