Bismuth(III) triflate-based catalytic direct opening of oleanolic hydroxy-gamma-lactones to afford 12-oxo-28-carboxylic acids

Jorge A. R. Salvador, Vânia M. Moreira, Rui M. A. Pinto, Ana S. Leal, Christophe Le Roux

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The bismuth(III) triflate-based catalytic direct opening of oleanolic hydroxy-g-lactones affords the corresponding 12-oxo-28-carboxylic acid derivatives, in both acetonitrile and dichloromethane, at reflux, in high yields. Participation of an in situ generated Brønsted acid species from bismuth (III) triflate is most likely involved in the reactionmechanism. Full structural elucidation of the products obtained has been performed by 1D and 2D NMR techniques.
Original languageEnglish
Pages (from-to)2637-2642
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume353
Issue number14-15
DOIs
Publication statusPublished - 10 Oct 2011

Fingerprint

Bismuth
Lactones
Carboxylic Acids
Methylene Chloride
Nuclear magnetic resonance
Derivatives
Acids
acetonitrile

Keywords

  • bismuth(III) triflate
  • hydroxylactones
  • oleanolic compounds
  • pentacyclic triterpenoids

Cite this

Salvador, Jorge A. R. ; Moreira, Vânia M. ; Pinto, Rui M. A. ; Leal, Ana S. ; Le Roux, Christophe. / Bismuth(III) triflate-based catalytic direct opening of oleanolic hydroxy-gamma-lactones to afford 12-oxo-28-carboxylic acids. In: Advanced Synthesis and Catalysis. 2011 ; Vol. 353, No. 14-15. pp. 2637-2642.
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Bismuth(III) triflate-based catalytic direct opening of oleanolic hydroxy-gamma-lactones to afford 12-oxo-28-carboxylic acids. / Salvador, Jorge A. R.; Moreira, Vânia M.; Pinto, Rui M. A.; Leal, Ana S.; Le Roux, Christophe.

In: Advanced Synthesis and Catalysis, Vol. 353, No. 14-15, 10.10.2011, p. 2637-2642.

Research output: Contribution to journalArticle

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