Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 14-15, Pages 2637-2642Publisher
WILEY-BLACKWELL
DOI: 10.1002/adsc.201100155
Keywords
bismuth(III) triflate; hydroxylactones; oleanolic compounds; 12-oxo-28-carboxylic acids; pentacyclic triterpenoids
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Funding
- Universidade de Coimbra
- Fundacao para a Ciencia e a Tecnologia [SFRH/BPD/45037/2008, SFRH/BD/41566/2007]
- Fundação para a Ciência e a Tecnologia [SFRH/BD/41566/2007, SFRH/BPD/45037/2008] Funding Source: FCT
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The bismuth(III) triflate-based catalytic direct opening of oleanolic hydroxy-gamma-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 Bronsted 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.
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