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Bismuth(III) Triflate‐Based Catalytic Direct Opening of Oleanolic Hydroxy‐γ‐lactones to Afford 12‐Oxo‐28‐carboxylic Acids
Author(s) -
Salvador Jorge A. R.,
Moreira Vânia M.,
Pinto Rui M. A.,
Leal Ana S.,
Le Roux Christophe
Publication year - 2011
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201100155
Subject(s) - chemistry , trifluoromethanesulfonate , catalysis , acetonitrile , oleanolic acid , dichloromethane , bismuth , carboxylic acid , medicinal chemistry , organic chemistry , solvent , medicine , alternative medicine , pathology
The bismuth(III) triflate‐based catalytic direct opening of oleanolic hydroxy‐γ‐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 reaction mechanism. Full structural elucidation of the products obtained has been performed by 1D and 2D NMR techniques.