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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
Published on: September 28, 2022
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Approaches to Cyclophane-Types of Cyclopeptide Alkaloids
Yuanhao Wang1, Madeleine M Joullié1
1Department of Chemistry, University of Pennsylvania, 231 S. 34th St., Philadelphia, PA 19104, USA.
Chemical Record (New York, N.Y.)
|March 3, 2021
Summary
Cyclopeptide alkaloids, cyclic depsipeptides with diverse bioactivities, are challenging to synthesize due to natural scarcity. This study explores efficient, stereocontrolled, and regioselective synthetic strategies for these complex natural products.
Area of Science:
- Natural Product Chemistry
- Organic Synthesis
- Medicinal Chemistry
Background:
- Cyclopeptide alkaloids are cyclic depsipeptides featuring macrocyclic systems (13- to 15-membered).
- Plants in the Rhamnacea family contain cyclopeptide alkaloids with reported pharmacological activities.
- Limited natural availability hinders comprehensive study of these compounds.
Purpose of the Study:
- To address the scarcity of cyclopeptide alkaloids by developing novel synthetic approaches.
- To explore diverse and efficient strategies for constructing these unique natural product structures.
- To achieve stereocontrolled and regioselective synthesis of cyclopeptide alkaloids.
Main Methods:
- Examination of various synthetic strategies for cyclopeptide alkaloid construction.
- Focus on methods enabling efficient, stereocontrolled, and regioselective synthesis.
- Review of established and novel synthetic pathways.
Main Results:
- Presentation of several typical strategies for cyclopeptide alkaloid synthesis.
- Demonstration of approaches for efficient and stereocontrolled macrocycle formation.
- Highlighting regioselective control in the synthesis of complex structures.
Conclusions:
- Novel synthetic strategies are crucial for overcoming the low natural availability of cyclopeptide alkaloids.
- Efficient, stereocontrolled, and regioselective methods are key to accessing these compounds.
- The presented strategies offer pathways for diverse construction of cyclopeptide alkaloid structures.
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