Concise Diastereoselective Total Synthesis of (±)-Parvistemonine A

Concise Diastereoselective Total Synthesis of (±)-Parvistemonine A: R. Matsuo, A. Miyashita, M. Kuwabara, S. Adachi, A. Matsuzawa, K. Sugita

Synlett 2020, 31, DOI: s10.1055/s-0040-1707283


In 2016, a series of new Stemona alkaloids were isolated from the roots of the medicinal plant Stemona parviflora. Parvistemonine A, whose structure was determined by NMR and MS analysis, was one of them. The roots of Stemona species have antitussive and insecticidal activities and have been used in folk medicine for thousands of years in East Asia. Furthermore, antinematode activity has been identified for several isolated Stemona alkaloids. Recently, the group of Professor Kazuyuki Sugita from Hoshi University (Tokyo, Japan) reported a concise and effective synthetic route for the title compound.

Professor Sugita said: “Utilization of Mukaiyama–Michael addition, aza-Wittig reaction, Paal–Knorr pyrrole synthesis, acid-mediated annulation, and Mitsunobu reaction enabled the total synthesis with the longest linear sequence being ten steps and with 19.6% overall yield. This concise synthesis might be applicable for the synthesis of derivatives for medicinal chemistry and for providing drug discovery scaffolds.”

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