Simone Borsoi, Luca Pozzi, Valerio Fasano, Andrea Citarella, Giovanni Macetti, Leonardo Lo Presti, Giuseppe Paladino, Umberto Ciriello, Daniele Passarella
ChemistrySelect 2025, 10, e202406175
Hydrogenation of the semisynthetic vinca alkaloid vinpocetine produces two epimers that have previously been investigated as chiral additives. However, the absence of a full characterization generated some ambiguities in their stereochemical identification. In this study, computational methods, NMR analysis, and X-ray crystallography were employed to clarify and revise the previously reported assignment. Additionally, various methods for the reduction of the 16,17-double bond of vinpocetine are explored. A comparative analysis of epimer formation ratios with the corresponding alcohols is presented, supported by a detailed NMR characterization of these previously unexplored alkaloids.