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Total synthesis of reblastatin
Iwona E Wrona1, Ana E Gabarda, Gwilherm Evano
1Department of Chemistry, Boston University, Boston, Massachusetts 02215, USA.
Journal of the American Chemical Society
|October 27, 2005
Summary
The enantioselective total synthesis of reblastatin was achieved. This study introduces novel methods for installing key structural features and forming the macrolactam ring.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Reblastatin is a complex natural product with potential biological activity.
- Efficient synthetic routes are crucial for accessing and studying such molecules.
Purpose of the Study:
- To develop a novel and enantioselective total synthesis of reblastatin.
- To establish new synthetic methodologies for complex molecule construction.
Main Methods:
- Hydrozirconation and transmetalation sequence for installing an E-trisubstituted olefin and C7 stereocenter.
- Intramolecular Buchwald-like amidation for macrolactam ring closure.
- Asymmetric synthesis strategies.
Main Results:
- Successful enantioselective total synthesis of reblastatin.
- Demonstration of a novel hydrozirconation-transmetalation-aldehyde addition sequence.
- First reported intramolecular Buchwald-like amidation for macrolactam formation.
Conclusions:
- The developed synthetic strategy is effective for constructing reblastatin.
- The novel methodologies employed offer valuable tools for complex molecule synthesis.
- This work provides a foundation for further biological evaluation of reblastatin.
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