Development of methodologies towards the total synthesis of okadaic acid
(2017)
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- Authors
- Supervisors
- Elias, Benjamin
- Abstract
- For the last decades, our laboratory has been interested in the development of new synthetic methodologies and their application to the total syntheses of natural products exhibiting biological activities. In this context, an investigation of the diastereoselective parameters of the ISMS reaction (for Intramolecular Silyl Modified Sakurai) triggered our interest. This first part was followed by its direct application to the synthesis of the C15-C27 domain of okadaic acid; a polycyclic ether produced by dinoflagellates. This natural compound exhibits a strong affinity for protein phosphatases 1 and 2A and is largely used as a probe in biochemistry. Since green chemistry became an important challenge for chemists all around the world, we decided to develop an electrochemical process leading to the formation of spiroketals. The electrochemical decarboxylation was applied to the synthesis of the C15-C27 domain of okadaic acid and offered a second route towards this fragment. Furthermore, we decided to extend this new and ecological methodology to the synthesis of the C1-C14 and C28-C38 in order to complete the syntheses of the okadaic acid domains.
- Affiliations
Citations
Body, J.-F. (2017). Development of methodologies towards the total synthesis of okadaic acid. https://hdl.handle.net/2078.5/39981