q&more
My watch list
my.chemie.de  
Login  

News

Synthesis of opium alkaloids using electric current

A selective electrochemical reaction offers a solution to a long-standing synthetic challenge

© Alexander Lipp

The Mainz-based chemists investigated the oxidative key step in the biosynthesis of thebaine, codeine, and morphine using a simple and self-made electrochemical cell.

02-Jul-2018: Researchers at Johannes Gutenberg University Mainz (JGU) have mastered a nearly 50-year-old challenge of electrosynthetic chemistry, namely the electrochemical synthesis of thebaine. The chemists had set themselves this difficult task within the framework of a collaboration with the University of Münster.

Thebaine is a component of the latex of the opium poppy and is named after the old designation of Luxor, i.e., the Ancient Egyptian city of Thebes. This opium alkaloid is the biosynthetic precursor of codeine and morphine and serves as the starting material for the industrial production of important pharmaceuticals, such as oxycodone or naloxone. The key step in the biosynthesis of thebaine, codeine, and morphine involves a reaction known as oxidative coupling. For decades, researchers have been trying to mimic this transformation in the laboratory. However, this oxidative coupling represents a considerable challenge because it can result in the formation of four different products, only one of which can be further converted into thebaine. Hence, in order to efficiently mimic this naturally occurring process, a highly selective reaction is mandatory.

For decades, chemists have attempted to accomplish a biomimetic synthesis of thebaine using conventional oxidants. However, large quantities of these often toxic reagents were required and undesired coupling products were obtained in most cases. Electrochemistry is a technique that involves the transfer of electrons to or from molecules on the surface of electrodes immersed in a solution. Using this method, it is possible to perform reagent-free oxidations. In fact, these environmentally benign processes only require electric current and avoid the production of chemical waste. So far, electrochemistry did not provide coupling products which could be transformed into thebaine, and its electrochemical synthesis remained a challenging task.

Alexander Lipp and Professor Till Opatz from the Institute of Organic Chemistry at JGU have now solved this long-standing problem. Their approach involved astute modification of the starting materials used in the oxidative coupling. With this, they have also paved the way for the future electrochemical synthesis of further opium alkaloids. Other participants involved in the project were Professor Siegfried R. Waldvogel, also from the Institute of Organic Chemistry at Mainz University, and Professor Hans J. Schäfer from the University of Münster. The project was undertaken under the aegis of the Advanced Lab for Electrochemistry and Electroorganic Synthesis (ELYSION), financed by the Carl Zeiss Foundation.

Original publication:
A. Lipp et al.; "A Regio‐ and Diastereoselective Anodic Aryl–Aryl Coupling in the Biomimetic Total Synthesis of (−)‐Thebaine"; Angewandte Chemie International Edition; 22 May 2018

Facts, background information, dossiers

  • oxidations
  • electroorganic synthesis
  • Opium
  • thebaine

More about Uni Mainz

  • News

    Scientists develop highly sensitive molecular optical pressure sensor

    Chemists at Johannes Gutenberg University Mainz (JGU) and at the Université de Montréal in Canada have developed a molecular system capable of very precise optical pressure measurements. The gemstone ruby served as the source of inspiration. However, the system developed by the team headed ... more

    Photoexcited graphene puzzle solved

    Light detection and control lies at the heart of many modern device applications, such as smartphone cameras. Using graphene as a light-sensitive material for light detectors can offer significant improvements with respect to materials being used nowadays. For example, graphene can detect l ... more

    Physicists propose a new method for monitoring nuclear waste

    New scientific findings suggest neutrino detectors may play an important role in ensuring better monitoring and safer storage of radioactive material in nuclear waste repository sites. Researchers at Johannes Gutenberg University Mainz (JGU) in Germany have made calculations to ascertain th ... more

q&more – the networking platform for quality excellence in lab and process

The q&more concept is to increase the visibility of recent research and innovative solutions, and support the exchange of knowledge. In the broad spectrum of subjects covered, the focus is on achieving maximum quality in highly innovative sectors. As a modern knowledge platform, q&more offers market participants one-of-a-kind networking opportunities. Cutting-edge research is presented by authors of international repute. Attractively presented in a high-quality context, and published in German and English, the original articles introduce new concepts and highlight unconventional solution strategies.

> more about q&more

q&more is supported by:

 

Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE