The synthesis of four isomers of p-coumaroylquinic acids was performed by esterification of p-acetylcoumaroylchloride with a suitably protected (-)-quinic acid. All isomers have been characterized by means of NMR spectroscopy and circular dichroism. Acyl migration was observed in the synthesis of 3-0-p-coumaroylquinic acid and 4-O-p-coumaroylquinic acid. Calculations on the most stable conformations of all isomers have also been performed to explain the acyl migration observed during the synthesis procedure.

Synthesis of p-coumaroylquinic acids and analysis of their interconversion

GUTIERREZ ORTIZ, Anggy Lusanna;BERTI, FEDERICO;FORZATO, Cristina
2017

Abstract

The synthesis of four isomers of p-coumaroylquinic acids was performed by esterification of p-acetylcoumaroylchloride with a suitably protected (-)-quinic acid. All isomers have been characterized by means of NMR spectroscopy and circular dichroism. Acyl migration was observed in the synthesis of 3-0-p-coumaroylquinic acid and 4-O-p-coumaroylquinic acid. Calculations on the most stable conformations of all isomers have also been performed to explain the acyl migration observed during the synthesis procedure.
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http://www.sciencedirect.com/science/article/pii/S0957416616304219
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11368/2904019
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