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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Published in:Synlett 2003-01, Vol.2003 (9)
Main Authors: Villalva-Servín, Nidia P., Laurent, Alain, Yap, Glenn P., Fallis, Alex G.
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container_title Synlett
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creator Villalva-Servín, Nidia P.
Laurent, Alain
Yap, Glenn P.
Fallis, Alex G.
description 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.
doi_str_mv 10.1055/s-2003-40358
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title A Direct Carbometallation-Stereoselective Cycloaddition-Ring Closing Metathesis Route to the Tricyclic ABC Core of Taxoids
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