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Total synthesis of (+)-schweinfurthins B and E
Joseph J Topczewski1, Jeffrey D Neighbors, David F Wiemer
1Department of Chemistry University of Iowa, Iowa City, Iowa 52242-1294, USA.
The Journal of Organic Chemistry
|August 25, 2009
Summary
The first total synthesis of (+)-schweinfurthin B, a cytotoxic agent, was achieved in 16 steps. This breakthrough provides scalable access to the natural product and clarifies its absolute stereochemistry.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Medicinal Chemistry
Background:
- (+)-Schweinfurthin B is a potent cytotoxic agent with differential activity.
- The complex structure of natural products presents significant synthetic challenges.
- Establishing absolute stereochemistry is crucial for understanding biological activity.
Purpose of the Study:
- To achieve the first total synthesis of (+)-schweinfurthin B.
- To develop an efficient and scalable synthetic route.
- To confirm the absolute stereochemistry of (+)-schweinfurthin B.
Main Methods:
- A 16-step linear synthesis from vanillin.
- Key steps included Shi epoxidation and BF(3).OEt(2)-initiated cascade cyclization.
- Utilized a methyl ether protecting group for benzylic alcohols, removed by DDQ oxidation.
Main Results:
- Successful total synthesis of (+)-schweinfurthin B.
- Established the absolute stereochemistry of the natural product.
- Developed a scalable route for biological studies and synthesized (+)-schweinfurthin E.
Conclusions:
- The first total synthesis of (+)-schweinfurthin B is reported.
- The synthetic route is efficient and provides scalable access to the compound.
- The absolute stereochemistry has been confirmed, enabling further biological investigation.
