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Total synthesis of (-)-FR901483
Ai-Jun Ma1, Yong-Qiang Tu, Jin-Bao Peng
1State Key Laboratory of Applied Organic Chemistry and Department of Chemistry, Lanzhou University , Lanzhou 730000, P. R. China.
Organic Letters
|June 28, 2012
Summary
Researchers achieved the total synthesis of the immunosuppressive alkaloid (-)-FR901483. This novel strategy efficiently constructs the complex azatricyclic core using a semipinacol rearrangement and intramolecular Schmidt reaction.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- (-)-FR901483 is a potent immunosuppressive alkaloid.
- Its complex azatricyclic structure presents a significant synthetic challenge.
Purpose of the Study:
- To develop a novel and efficient total synthesis of (-)-FR901483.
- To explore new synthetic methodologies for constructing complex alkaloids.
Main Methods:
- Total synthesis of (-)-FR901483.
- Utilized a semipinacol-type rearrangement.
- Employed an intramolecular Schmidt reaction on an azido cyclohexanone derivative.
Main Results:
- Successfully constructed the azatricyclic core of (-)-FR901483.
- Demonstrated the efficacy of the chosen synthetic strategy.
Conclusions:
- The described synthetic route offers a distinctive and competitive approach to (-)-FR901483.
- The methodology is applicable to the synthesis of other complex natural products.
