HAL will be down for maintenance from Friday, June 10 at 4pm through Monday, June 13 at 9am. More information
Skip to Main content Skip to Navigation
Journal articles

Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives

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
Complete list of metadata

https://hal-polytechnique.archives-ouvertes.fr/hal-01355946
Contributor : Denis Roura Connect in order to contact the contributor
Submitted on : Wednesday, August 24, 2016 - 3:04:16 PM
Last modification on : Thursday, December 9, 2021 - 2:26:02 PM

Links full text

Identifiers

Citation

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⟩

Share

Metrics

Record views

118