Related Experiment Video
Updated: Jun 8, 2026
09:47
Isolation and Compositional Analysis of Plant Cuticle Lipid Polyester Monomers
Published on: November 22, 2015
Total synthesis of (-)-callipeltoside A
Thomas R Hoye1, Michael E Danielson, Aaron E May
1Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States. hoye@umn.edu
The Journal of Organic Chemistry
|October 12, 2010
Summary
Chemists achieved the total synthesis of (-)-callipeltoside A. A novel dual macrolactonization/pyran hemiketal formation reaction was developed to construct the macrocyclic core of this complex natural product.
Area of Science:
- Organic Chemistry
- Natural Product Synthesis
Background:
- (-)-callipeltoside A is a complex natural product with potential biological significance.
- Previous synthetic efforts faced challenges in constructing the core macrocycle.
Purpose of the Study:
- To achieve the first total synthesis of (-)-callipeltoside A.
- To develop a novel synthetic strategy for constructing the macrocyclic core.
Main Methods:
- Development of a dual macrolactonization/pyran hemiketal formation reaction.
- Utilized ring-closing metathesis (RCM) and relay ring-closing metathesis (RRCM) in initial approaches.
Main Results:
- Successful total synthesis of (-)-callipeltoside A.
- The novel dual reaction efficiently formed the core macrocycle, overcoming issues with acylketene intermediates.
- Exploration of RCM and RRCM strategies provided insights into synthetic challenges.
Conclusions:
- The developed dual macrolactonization/pyran hemiketal formation reaction is an effective method for synthesizing the macrocyclic core of (-)-callipeltoside A.
- This synthesis represents a significant advancement in natural product chemistry.
