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Theses Year : 2008

Studies towards the synthesis of the abc tricycle of taxol

Vers la synthèse du tricycle ABC du Taxol

Cong Ma
  • Function : Author

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.
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Dates and versions

pastel-00004596 , version 1 (28-01-2009)

Identifiers

  • HAL Id : pastel-00004596 , version 1

Cite

Cong Ma. Studies towards the synthesis of the abc tricycle of taxol. Chemical Sciences. Ecole Polytechnique X, 2008. English. ⟨NNT : ⟩. ⟨pastel-00004596⟩

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