Ma, Cong (2008) Studies towards the synthesis of the abc tricycle of taxol. PhD thesis Chimie, Ecole Polytechnique, EP/X.
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Abstract
Taxol®, isolated from the bark of the Pacific yew tree (Taxus brevifolia Nutt.), is a very effective drug in the treatment of cancers worldwide. Six total syntheses and numerous synthetic works have been published since its discovery. We planned a semi-convergent total synthesis of taxol, which could be synthesized from an intermediate in Holton’s synthesis. The A ring would be installed at a late stage by anintramolecular pinacolic condensation on a diketone. Bicycle BC would be formed by a ring-closing metathesis on a diene, which would be prepared by addition of a vinyllithium (Synthon 2) to an aldehyde (Synthon 1).
In the course of our studies, model BC ring-systems of taxol, which lack the oxygenated substituent at C7 and the alkyne moiety, have been efficiently synthesized. Comparison of
ring-closing metatheses with similar substrates was thoroughly studied. We are currently preparing the synthesis of the ABC tricycle of taxol with all the required functionalities.
| Item Type: | PhD Thesis (PhD) |
|---|---|
| PhD Supervisor: | Prunet, Joëlle |
| Date: | 12 November 2008 |
| Board of examiners: | Arseniyadis, Siméon and Kouklovsky, Cyrille and Nay, Bastien and Pancrazi, Ange |
| Ecole Doctorale: | ED 447 ECOLE DOCTORALE DE L'ECOLE POLYTECHNIQUE |
| Discipline: | Chimie |
| Collection (Fonds): | Ecole Polytechnique (EP/X) |
| Institution: | EP/X |
| Department: | Ecole Polytechnique |
| Subjects: | 6. Chemistry, Physical Chemistry and Chemical Engineering |
| ID Code: | 4596 |
| Deposited By: | Cong Ma |
| Deposited On: | 28 January 2009 |
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