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Total Synthesis of Pulvomycin D
Lukas Fritz1, Sebastian Wienhold1, Sabrina Hackl1
1School of Natural Sciences, Department of Chemistry and Catalysis Research Center, Technische Universität München, Lichtenbergstrasse 4, 85747, Garching, Germany.
This study details the first total synthesis of pulvomycin D, a complex natural product. The strategy employed key reactions like aldol, Yamaguchi esterification, Heck, and Peterson elimination for its construction.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- Pulvomycin class natural products possess complex structures.
- Total synthesis provides access to these valuable compounds for further study.
Purpose of the Study:
- To achieve the first total synthesis of pulvomycin D.
- To develop a robust synthetic route applicable to the pulvomycin class.
Main Methods:
- Convergent synthesis strategy.
- Key bond formations via aldol reaction and Yamaguchi esterification.
- Lactone ring closure using Heck reaction.
- Final deprotection and olefin formation via Peterson elimination.
Main Results:
- Successful construction of the 40-carbon skeleton of pulvomycin D.
- Efficient assembly of molecular fragments.
- Completion of the 22-membered lactone ring.
Conclusions:
- The presented synthetic route is effective for pulvomycin D.
- This work provides a foundation for synthesizing other pulvomycin analogues.
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