A Direct Carbometallation-Stereoselective Cycloaddition-Ring Closing Metathesis Route to the Tricyclic ABC Core of Taxoids

Nidia P. Villalva-Servín; Alain Laurent; Glenn P. A. Yap; Alex G. Fallis

doi:10.1055/s-2003-40358

LETTER

A Direct Carbometallation-Stereoselective Cycloaddition-Ring Closing Metathesis Route to the Tricyclic ABC Core of Taxoids

Nidia P. Villalva-Servín, Alain Laurent^b, Glenn P. A. Yap, Alex G. Fallis*^a
^a Centre for Research in Biopharmaceuticals, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N 6N5, Canada
Fax: +1(613)5625170; e-Mail: afallis@science.uottawa.ca;
^b Aegera Therapeutics Inc., Montreal, Quebec, H3E 1A8, Canada

Abstract

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Abstract

The synthesis of the tricyclic ABC ring-system of Taxol^® (paclitaxel) is described. This direct route involves sequential reactions employing the carbometallation of a propargyl alcohol, followed by a cis-alkene tether controlled stereoselective intramolecular Diels-Alder reaction to generate the AB-ring system and ring closing metathesis (RCM) of the pendant allyl substituents to construct the C ring.

Key words

carbometallation - Diels-Alder - taxanes - ring closing metathesis (RCM)

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References

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