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Total Synthesis of (+)-Pleuromutilin
Elliot P Farney1, Sean S Feng1, Felix Schäfers1
1The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
Journal of the American Chemical Society
|January 12, 2018
Summary
An 18-step synthesis of the antibiotic (+)-pleuromutilin was developed using key stereoselective reactions. This breakthrough enables the creation of novel mutilin antibiotics for future therapeutic applications.
Area of Science:
- Organic Synthesis
- Medicinal Chemistry
- Antibiotic Development
Background:
- Pleuromutilin is a natural antibiotic with a unique tetracyclic diterpene core.
- Existing synthetic routes to pleuromutilin are often lengthy and complex.
- Development of efficient synthetic strategies is crucial for accessing novel analogs.
Purpose of the Study:
- To disclose a novel and efficient 18-step synthesis of the antibiotic (+)-pleuromutilin.
- To establish key stereocenters using advanced synthetic methodologies.
- To provide a platform for the synthesis of new mutilin-based antibiotics.
Main Methods:
- Employed an 18-step synthetic sequence.
- Utilized samarium(II) iodide (SmI2)-mediated cyclization for constructing the eight-membered ring.
- Implemented a stereospecific transannular [1,5]-hydrogen atom transfer to control C10 stereochemistry.
Main Results:
- Successfully synthesized (+)-pleuromutilin in 18 steps.
- Achieved high stereoselectivity in the SmI2-mediated cyclization step.
- Demonstrated the ability to prepare (+)-12-epi-pleuromutilin using the same strategy.
Conclusions:
- The developed synthetic route is efficient and stereocontrolled.
- The key cyclization and hydrogen transfer reactions are robust.
- This synthetic approach facilitates the exploration of new mutilin antibiotic derivatives.
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