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

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 gener...

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Bibliographic Details
Published in:Synlett 2003-01, Vol.2003 (9)
Main Authors: Villalva-Servín, Nidia P., Laurent, Alain, Yap, Glenn P., Fallis, Alex G.
Format: Article
Language:English
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Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2003-40358