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Vers la synthèse totale de l'acide okadaïque
| Content Provider | Semantic Scholar |
|---|---|
| Author | Dochain, Simon |
| Copyright Year | 2015 |
| Abstract | Leading member of the diarrheic shellfish poisoning family, okadaic acid, a natural polyether produced by dinoflagellates, has been shown to be a very interesting biochemical tool. Its potent and selective inhibition of protein phosphatases 1 and 2A (PP1 and PP2A) made it one of the most used mechanistic probe for understanding those enzymes related processes. During this PhD thesis, we undertook the synthesis of okadaic acid based on a three fragments disconnection. The core of the Western fragment was built with the help of allylselenide chemistry, who could easily be converted to allyllithium after addition of n-BuLi. Then, the ISMS methodology allowed us to get a racemic model of the first cycle of the Central core. Finally, two different methodologies were used to synthetize the Eastern fragment of the polyether. Taddei-Ricci modified conditions, followed by photochemical Suarez oxidation, were the key steps of the first route and electrochemical oxidation of a malonic acid were used as a key step in the second route. |
| File Format | PDF HTM / HTML |
| Alternate Webpage(s) | https://dial.uclouvain.be/downloader/downloader.php?datastream=PDF_01&disclaimer=ebef0fa8dd6d56a4a8a4af9a35c82ef2204bed8c52febaa1d0fff8bf6fb4c7e2&pid=boreal:165869 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
