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

Research output: Journal article publicationJournal articleAcademic researchpeer-review

14 Citations (Scopus)

Abstract

KGaA, Weinheim. 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 16 a,b and 18 b 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.
Original languageEnglish
Pages (from-to)6891-6898
Number of pages8
JournalChemistry - A European Journal
Volume22
Issue number20
DOIs
Publication statusPublished - 10 May 2016
Externally publishedYes

Keywords

  • cyclooctenes
  • enyne
  • metathesis
  • synthesis design
  • taxanes

ASJC Scopus subject areas

  • Chemistry(all)

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