Transformation of strictosamide to vincoside lactam by acid catalysis

AimTo identify the structure of the acid-catalyzed product of strictosamide and explore the reaction mechanism.MethodsThe acid-catalyzed reaction process of strictosamide was monitored by HPLC, and a macroporous resin was used to purify the reaction solution. The structure of the product was confirmed by MS, NMR, and ROESY spectra.ResultsThe acid-catalyzed transformation yield from strictosamide to vincoside lactam was 52%.ConclusionThe reaction mechanism of the transformation from strictosamide to vincoside lactam may be related to the stability of the three-dimensional configuration of the compound. These results offer a new way to obtain vincoside lactam from the widely distributed indole alkaloid strictosamide by acid-catalysis.