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Total Synthesis of the Reported Structure of Neaumycin B
1Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, United States.
Journal of the American Chemical Society
|August 10, 2023
Summary
Researchers achieved the stereoselective total synthesis of neaumycin B, a macrolide natural product. This synthesis utilized a novel nickel-catalyzed cross-coupling and spiroketalization strategy for efficient core construction.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Macrolide Chemistry
Background:
- Neaumycin B is a complex macrolide natural product with potential biological significance.
- Total synthesis provides access to complex natural products for further study and analog development.
Purpose of the Study:
- To report the stereoselective total synthesis of neaumycin B.
- To develop and apply a novel synthetic strategy for constructing the macrolide core.
Main Methods:
- Stereoselective total synthesis of neaumycin B.
- Gram-scale nickel-catalyzed reductive cross-coupling and spiroketalization.
- X-ray crystallography for stereochemical verification.
Main Results:
- Successful synthesis of neaumycin B in 2.3% overall yield on a 90 mg scale.
- Efficient construction of the spiroketal core using the developed tactic.
- Unambiguous verification of stereostructures for key segments via X-ray crystallography.
Conclusions:
- The developed synthetic route provides a viable pathway to neaumycin B.
- The nickel-catalyzed tactic is effective for constructing complex spiroketal cores.
- X-ray crystallography confirms the stereochemical integrity of the synthetic product.
