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Electrochemically Enabled One-Pot Multistep Synthesis of C19 Androgen Steroids
Florian Sommer1,2, C Oliver Kappe1,2, David Cantillo1,2
1Institute of Chemistry, University of Graz, Heinrichstrasse 28, 8010, Graz, Austria.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 8, 2021
Summary
Sustainable electrochemical methods offer a greener alternative for synthesizing C19 steroids from corticosteroids. This approach avoids harsh chemicals and extensive purification, enabling efficient androgen production.
Area of Science:
- Organic Chemistry
- Electrochemistry
- Steroid Synthesis
Background:
- Conventional synthesis of C19 androgens from corticosteroids generates significant waste and requires extensive purification.
- Existing methods for C17 side chain removal are often inefficient and environmentally taxing.
Purpose of the Study:
- To develop mild, safe, and sustainable electrochemical strategies for C19 steroid synthesis.
- To establish reagent and catalyst-free protocols for androgen preparation.
- To demonstrate atom-economic procedures for synthesizing saturated androgens.
Main Methods:
- Anodic oxidation for C17 side chain removal from corticosteroids.
- One-pot, multistep procedures for androgen synthesis.
- Simultaneous anodic C17 side chain cleavage and cathodic catalytic hydrogenation.
Main Results:
- A reagent and catalyst-free protocol for corticosteroid C17 side chain removal via anodic oxidation was established.
- Successful one-pot, multistep synthesis of androgen steroids was achieved.
- Simultaneous electrochemical reactions enabled a highly atom-economic synthesis of saturated androgens.
Conclusions:
- Electrochemical strategies provide a sustainable and efficient alternative for C19 steroid synthesis.
- The developed methods minimize waste and purification steps, aligning with green chemistry principles.
- This work offers convenient and atom-economic routes to valuable androgen steroids.
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
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