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Updated: Jul 26, 2026
14:18
A Strategy for Sensitive, Large Scale Quantitative Metabolomics
Published on: May 27, 2014
A concise synthesis of the octalactins
Paul T O'Sullivan1, Wilm Buhr, Mary Ann M Fuhry
1Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
Journal of the American Chemical Society
|February 20, 2004
Summary
The total synthesis of octalactins A and B was successfully achieved using a 15-step process. This research presents a novel synthetic route for these complex marine natural products.
Area of Science:
- Organic Chemistry
- Total Synthesis
- Marine Natural Products
Background:
- Octalactins A and B are complex marine natural products with potential biological activities.
- Previous synthetic efforts have been limited, highlighting the need for efficient routes.
Purpose of the Study:
- To achieve the first total synthesis of octalactins A and B.
- To develop a concise and efficient synthetic strategy.
Main Methods:
- The synthesis employed a 15-step longest linear sequence starting from commercially available materials.
- Key reactions included the Paterson-Aldol reaction, methylenation, Claisen rearrangement, and enzyme-mediated deprotection.
Main Results:
- The total synthesis of octalactins A and B was accomplished with a 10% overall yield.
- The core unsaturated medium-ring lactone was efficiently constructed.
Conclusions:
- The developed synthetic route provides a viable method for accessing octalactins A and B.
- The strategy showcases the utility of specific reactions in constructing complex lactone structures.
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