Skip to Main content Skip to Navigation
Theses

Studies towards the synthesis of the abc tricycle of taxol

Cong Ma
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.
Document type :
Theses
Complete list of metadatas

Cited literature [8 references]  Display  Hide  Download

https://pastel.archives-ouvertes.fr/pastel-00004596
Contributor : Ecole Polytechnique <>
Submitted on : Wednesday, January 28, 2009 - 8:00:00 AM
Last modification on : Wednesday, January 28, 2009 - 8:00:00 AM
Long-term archiving on: : Friday, September 10, 2010 - 1:19:39 PM

Identifiers

  • HAL Id : pastel-00004596, version 1

Collections

Citation

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

Share

Metrics

Record views

257

Files downloads

1569