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Medium ring ethers by ring expansion-ring contraction: synthesis of lauthisan
Mark J Coster1, James J De Voss
1Department of Chemistry, University of Queensland, Brisbane 4072, Australia.
Organic Letters
|August 31, 2002
Summary
A novel synthetic route constructs medium-ring ethers via halo-O,S-acetal ring expansion and subsequent Ramberg-Bäcklund contraction, extruding sulfur. This method efficiently synthesizes cis- and trans-lauthisan.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Heterocyclic Chemistry
Background:
- Medium-ring ethers present synthetic challenges.
- Existing methods for medium-ring ether synthesis are limited.
Purpose of the Study:
- To develop a general and efficient method for constructing medium-ring ethers.
- To demonstrate the utility of this new methodology in synthesizing specific natural products.
Main Methods:
- Ring expansion of halo-O,S-acetals.
- Ramberg-Bäcklund reaction for ring contraction.
- Concomitant sulfur atom extrusion.
Main Results:
- Successful development of a new general method for medium-ring ether synthesis.
- Application of the method for the synthesis of cis- and trans-lauthisan.
- Demonstration of the reaction's efficiency and versatility.
Conclusions:
- The developed methodology provides a facile route to medium-ring ethers.
- This approach is valuable for the synthesis of complex molecules like lauthisan.
- The sulfur extrusion is a key feature of this novel transformation.