Synthesis of the Hexahydropyrrolo-[3,2-c]-quinoline Core Structure and Strategies for Further Elaboration to Martinelline, Martinellic Acid, Incargranine B, and Seneciobipyrrolidine

Molecules. 2021 Jan 11;26(2):341. doi: 10.3390/molecules26020341.

Abstract

Natural products are rich sources of interesting scaffolds possessing a plethora of biological activity. With the isolation of the martinella alkaloids in 1995, namely martinelline and martinellic acid, the pyrrolo[3,2-c]quinoline scaffold was discovered. Since then, this scaffold has been found in two additional natural products, viz. incargranine B and seneciobipyrrolidine. These natural products have attracted attention from synthetic chemists both due to the interesting scaffold they contain, but also due to the biological activity they possess. This review highlights the synthetic efforts made for the preparation of these alkaloids and formation of analogues with interesting biological activity.

Keywords: hexahydropyrrolo-[3,2-c]-quinoline; incargranine B; martinellic acid; martinelline; natural product synthesis; scaffold; seneciobipyrrolidine.

Publication types

  • Review

MeSH terms

  • Alkaloids / chemical synthesis*
  • Bignoniaceae / chemistry
  • Biological Products / chemical synthesis
  • Chemistry Techniques, Synthetic / methods
  • Pyrroles / chemical synthesis*
  • Pyrrolidines / chemical synthesis*
  • Quinolines / chemical synthesis*

Substances

  • Alkaloids
  • Biological Products
  • Pyrroles
  • Pyrrolidines
  • Quinolines
  • incargranine B
  • martinellic acid
  • martinelline