The Meyer-Schuster rearrangement: a new synthetic strategy leading to prostaglandins and their drug analogs, Bimatoprost and Latanoprost

Giuseppe Zanoni, Alessandro D'Alfonso, Alessio Porta, Lazzaro Feliciani, Steven Patrick Nolan, Giovanni Vidari

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)

Abstract

Gold(I) mediated Meyer Schuster rearrangement for the installation of the 'lower' side chain of prostaglandins and their analogs has been developed. This Au-mediated rearrangement, featuring a low catalyst loading and mild reaction conditions, has been demonstrated to be an efficient alternative to the standard Horner-Wadsworth-Emmons reaction in prostaglandin chemistry. Moreover, the present results provide a new synthetic process leading to pharmacologically active prostanoids: Latanoprost and Bimatoprost, that continue to hold key positions in the anti-glaucoma drug market. (C) 2010 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)7472-7478
Number of pages7
JournalTetrahedron
Volume66
Issue number38
DOIs
Publication statusPublished - 18 Sept 2010

Keywords

  • Anti-glaucoma drug
  • Meyer-Schuster rearrangement
  • Gold Chemistry
  • Prostanoids syntheses
  • Total synthesis
  • GOLD
  • KETONES
  • CATALYSIS

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