Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives

Cong Ma; Aurélien Letort; Rémi Aouzal; Antonia Wilkes; Gourhari Maiti; Louis J. Farrugia; Louis Ricard; Joëlle Prunet

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.

Document type :

Journal articles

Domain :

Chemical Sciences / Organic chemistry

Complete list of metadatas

https://hal-polytechnique.archives-ouvertes.fr/hal-01355946
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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

Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives

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Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives

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