Asymmetric Total Synthesis of Four Stemona Alkaloids

Org Lett. 2023 Apr 7;25(13):2213-2217. doi: 10.1021/acs.orglett.3c00349. Epub 2023 Mar 26.

Abstract

Asymmetric total syntheses of four Stemona alkaloids were accomplished, and among them, bisdehydrostemoninine A and stemoninine A were synthesized for the first time. Notably, these four alkaloids were divergently synthesized from a common tetracyclic intermediate, which was easily obtained from a known compound. Friedel-Crafts acylation was employed to introduce the key side chain at position C3 of Stemona alkaloids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acylation
  • Alkaloids* / chemistry
  • Heterocyclic Compounds, 3-Ring
  • Molecular Structure
  • Stemonaceae* / chemistry

Substances

  • Alkaloids
  • Heterocyclic Compounds, 3-Ring
  • bisdehydrostemoninine A