First diastereoselective synthesis of methyl caffeoyl- and feruloyl-muco-quinates.
We report on a diastereoselective synthesis of six derivatives of caffeoyl- and feruloyl-muco-quinic acids. All the muco-quinic acid derivatives were obtained in excellent yield in five steps starting from quinic acid, caffeic acid and ferulic acid. Allyl ether protection of trans-hydroxy cinnamic acids was here introduced to chlorogenic acids synthesis. We show that muco-quinic acid derivatives, which are formally diastereoisomers of chlorogenic acids, can be readily distinguished by their tandem mass spectra.
Jacobs University Bremen, Bremen, Germany.
Rakesh
R
Jaiswal
Michael H
MH
Dickman
Nikolai
N
Kuhnert
D002109:Caffeic Acids / Q000737:chemistry*; D003373:Coumaric Acids / Q000737:chemistry*; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D011801:Quinic Acid / Q000138:chemical synthesis*; D013237:Stereoisomerism
D002109:Caffeic Acids; D003373:Coumaric Acids; D011801:Quinic Acid; C004999:ferulic acid; C040048:caffeic acid