Ten-Step Total Synthesis of (-)-Andranginine

Org Lett. 2022 Sep 23;24(37):6880-6883. doi: 10.1021/acs.orglett.2c02927. Epub 2022 Sep 13.

Abstract

The total synthesis of the indole alkaloid (-)-andranginine has been achieved in 10 steps. Key reactions of the synthesis include a nucleophilic addition of acetylenyl anion to chiral N-sulfinyl imine, an intramolecular N-alkylation reaction to close the C ring, and a dienyne metathesis cascade reaction to construct the DE rings. Meanwhile, 16-epi-(-)-andranginine was also obtained with the developed strategy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Imines*
  • Indole Alkaloids*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Imines
  • Indole Alkaloids
  • andranginine