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Published on: January 13, 2017
Total synthesis and structural revision of lucentamycin A
Sujeewa Ranatunga1, Chih-Hang Anthony Tang, Chih-Chi Andrew Hu
1Drug Discovery Department, H. Lee Moffitt Cancer Center and Research Institute, Tampa, Florida 33612, United States.
The Journal of Organic Chemistry
|October 9, 2012
Summary
The first total synthesis of lucentamycin A confirms its unique 4-ethylidene-3-methylproline subunit has an E geometry, correcting the original Z configuration assignment. This marine natural product synthesis advances peptide chemistry.
Area of Science:
- Marine natural product chemistry
- Organic synthesis
- Peptide chemistry
Background:
- Lucentamycin A is a marine peptide natural product containing a unique 4-ethylidene-3-methylproline (Emp) subunit.
- Previous synthetic efforts cast doubt on the proposed structure of lucentamycin A and its Emp residue.
Purpose of the Study:
- To report the first total synthesis of lucentamycin A.
- To definitively determine the stereochemistry of the ethylidene substituent in the Emp subunit.
Main Methods:
- Total synthesis of lucentamycin A.
- Development of a novel synthetic strategy for the (E)-Emp subunit starting from Garner's aldehyde.
Main Results:
- The total synthesis successfully confirmed the structure of lucentamycin A.
- The ethylidene substituent in the Emp subunit was determined to possess E geometry, contradicting the initially proposed Z configuration.
Conclusions:
- The first total synthesis validates the E configuration of the ethylidene substituent in the Emp subunit of lucentamycin A.
- This work clarifies the structural ambiguity surrounding this marine natural product and provides a new synthetic route for the key Emp subunit.
