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Total synthesis of (+)-11,11'-dideoxyverticillin A
Justin Kim1, James A Ashenhurst, Mohammad Movassaghi
1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA 02139, USA.
Science (New York, N.Y.)
|April 11, 2009
Summary
Researchers achieved the first total synthesis of the complex fungal alkaloid (+)-11,11'-dideoxyverticillin A. This breakthrough provides a new strategy for synthesizing related epidithiodiketopiperazine natural products.
Area of Science:
- Natural Product Chemistry
- Organic Synthesis
- Marine Microbiology
Background:
- The fungal metabolite (+)-11,11'-dideoxyverticillin A is a cytotoxic alkaloid.
- It belongs to the dimeric epidithiodiketopiperazine family, known for their structural complexity.
- Despite being known for decades, no member of this family has been synthesized totally.
Purpose of the Study:
- To achieve the first enantioselective total synthesis of (+)-11,11'-dideoxyverticillin A.
- To develop a synthetic strategy inspired by the proposed biosynthetic pathway.
- To establish a method for synthesizing other complex epidithiodiketopiperazines.
Main Methods:
- Enantioselective total synthesis strategy.
- Advanced-stage tetrahydroxylation and tetrathiolation reactions.
- Mild introduction of the epidithiodiketopiperazine core.
Main Results:
- A concise and enantioselective total synthesis of (+)-11,11'-dideoxyverticillin A was successfully accomplished.
- Highly stereo- and chemoselective reactions were developed for key transformations.
- A mild final step strategy for the sensitive epidithiodiketopiperazine core was established.
Conclusions:
- The total synthesis of (+)-11,11'-dideoxyverticillin A was achieved, overcoming a long-standing challenge.
- The developed synthetic strategy, inspired by biosynthesis, is effective for this alkaloid family.
- This work opens avenues for the synthesis of other complex dimeric epidithiodiketopiperazines.
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