Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives

Cong Ma 1 Aurélien Letort 2 Rémi Aouzal 1 Antonia Wilkes 2 Gourhari Maiti 1 Louis J. Farrugia 2 Louis Ricard 3 Joëlle Prunet 2
1 DCSO - Laboratoire de synthèse organique
2 WestCHEM
3 LCM - Laboratoire de chimie moléculaire
Abstract : Tricyclic isotaxane and taxane derivatives have been synthesized by a very efficient cascade ring-closing dienyne metathesis (RCDEYM) reaction, which formed the A and B rings in one operation. When the alkyne is present at C13 (with no neighboring gem-dimethyl group), the RCEDYM reaction leads to 14,15-isotaxanes 16a,b and 18b with the gem-dimethyl group on the A ring. If the alkyne is at the C11 position (and thus flanked by a gem-dimethyl group), RCEDYM reaction only proceeds in the presence of a trisubstituted olefin at C13, which disfavors the competing diene ring-closing metathesis reaction, to give the tricyclic core of Taxol 44.
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Submitted on : Wednesday, August 24, 2016 - 3:04:16 PM
Last modification on : Thursday, June 20, 2019 - 10:14:01 AM

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Cong Ma, Aurélien Letort, Rémi Aouzal, Antonia Wilkes, Gourhari Maiti, et al.. Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives. Chemistry - A European Journal, Wiley-VCH Verlag, 2016, 22 (20), pp.6891-6898. ⟨10.1002/chem.201600592⟩. ⟨hal-01355946⟩

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