Synthesis of BC ring-systems of Taxol by ring-closing metathesis

D Bourgeois, J Mahuteau, A Pancrazi, Steven Patrick Nolan, J Prunet

Research output: Contribution to journalArticlepeer-review

48 Citations (Scopus)

Abstract

Highly functionalized BC ring-systems of Taxol((R)) having the required chemistry for the C1, C2 and C8 centers have been syn the sized using a ring-closing metathesis (RCM) reaction as the key step. Silylene 26 and acetonide 27 were obtained in excellent yields with Schrock's and our recently reported catalyst. In the case of carbonate 23, a trans cyclooctene was formed when using Grubbs' catalyst, indicating that RCM does nut always proceed to completion of thermodynamic equilibrium.

Original languageEnglish
Pages (from-to)869-882
Number of pages14
JournalSynthesis
Issue number6
Publication statusPublished - Jun 2000

Keywords

  • cyclooctenes
  • cyclization
  • metathesis
  • olefin
  • Taxol
  • ruthenium
  • molybdenum
  • OLEFIN METATHESIS
  • IMIDAZOLIN-2-YLIDENE LIGANDS
  • TAXANE PRECURSOR
  • RUTHENIUM
  • CATALYSTS
  • RUCL2(=CHR')(PR(3))(2)
  • COMPLEXES
  • CHEMISTRY
  • PRODUCTS
  • TAXOTERE

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