Studies towards the synthesis of the abc tricycle of taxol

Vers la synthèse du tricycle ABC du Taxol

Cong Ma

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.

Le Taxol

Domaines: Chimie

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