Cyclopropanation Strategies in Recent Total Syntheses
Christian Ebner1, Erick M Carreira1
1Eidgenössische Technische Hochschule Zürich , Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland.
Chemical Reviews
|May 4, 2017
Summary
Synthesizing complex molecules with cyclopropane rings is challenging. This review covers key cyclopropanation methods and strategies for incorporating these motifs in total synthesis, aiding chemists in creating novel natural products.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Medicinal Chemistry
Background:
- Cyclopropane-containing molecules are prevalent in natural products and pharmaceuticals.
- The synthesis of complex molecular architectures featuring cyclopropanes poses significant challenges due to their inherent ring strain and unique reactivity.
Purpose of the Study:
- To review and highlight strategic considerations for the introduction of the cyclopropane motif in recent total syntheses.
- To provide an overview of important and widely used cyclopropanation techniques.
- To discuss elegant approaches and solutions for synthesizing cyclopropane-containing natural products and intermediates.
Main Methods:
- Literature review of recent total syntheses incorporating cyclopropane motifs.
- Analysis of established and emerging cyclopropanation methodologies.
- Case studies showcasing strategic implementation of cyclopropane synthesis.
Main Results:
- An overview of key cyclopropanation techniques, including carbene/carbenoid additions and intramolecular cyclizations.
- Discussion of strategic decisions in total synthesis that leverage cyclopropane formation.
- Examples of successful synthesis of complex natural products and versatile cyclopropane intermediates.
Conclusions:
- Strategic planning is crucial for the efficient synthesis of cyclopropane-containing complex molecules.
- A diverse toolkit of cyclopropanation methods enables access to a wide range of cyclopropane motifs.
- Cyclopropanes serve as valuable building blocks and key structural elements in synthetic chemistry.
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