Related Experiment Video
Updated: Feb 25, 2026
09:35
Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
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Total Synthesis and Structural Assignment of Curvicollide C
Valeska von Kiedrowski1, Florian Quentin1, Martin Hiersemann1
1Fakultät für Chemie und Chemische Biologie, Technische Universität Dortmund , 44227 Dortmund, Germany.
Organic Letters
|August 2, 2017
Summary
The first total synthesis of (+)-curvicollide C, a fungal polyketide, was achieved using cross-metathesis and Julia-Kocienski olefination. This study also proposes a full structural assignment for the related (-)-curvicollide C.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
- Mycology
Background:
- Curvicollide C is a unique polyketide isolated from fungi.
- The complex structure of curvicollides presents a significant synthetic challenge.
- Understanding the chemical diversity of fungal metabolites is crucial for drug discovery.
Purpose of the Study:
- To achieve the first total synthesis of (+)-curvicollide C.
- To develop efficient synthetic strategies for constructing polyketide natural products.
- To elucidate the complete structure of (-)-curvicollide C.
Main Methods:
- Ternary-convergent synthetic design.
- Cross-metathesis for 1,3-diene synthesis.
- Julia-Kocienski olefination for fragment coupling.
Main Results:
- Successful total synthesis of (+)-curvicollide C.
- Demonstration of the utility of cross-metathesis and Julia-Kocienski olefination in complex molecule synthesis.
- Proposed full structural assignment for (-)-curvicollide C.
Conclusions:
- The developed synthetic route provides access to (+)-curvicollide C.
- The study highlights the power of modern synthetic methodologies in natural product chemistry.
- Further investigation into the biological activity of curvicollides is warranted.
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