Biomimetic synthesis of 6-substituted dihydrobenzophenanthridine alkaloids based on visible-light promoted radical addition reaction

Nat Prod Res. 2022 Jan;36(1):341-347. doi: 10.1080/14786419.2020.1784171. Epub 2020 Jun 27.

Abstract

Oxidative C-H functionalization of dihydrobenzophenanthridines catalyzed by dihydrobenzophenanthridine oxidase (DBOX) is believed to be the key step involved in the biosynthetic pathway of some novel 6-substituted benzophenanthridine alkaloids. In this study, a visible-light promoted biomimetic synthesis of 6-substituted benzophenanthridines was reported under photoredox-neutral conditions. α-Amino radical that derived from dihydrobenzophenanthridines was supposed to be the key intermediate in this visible-light promoted radical-type Michael addition reaction.

Keywords: Benzophenanthridine; biomimetic synthesis; photoredox catalysis; radical addition; visible light.

MeSH terms

  • Alkaloids*
  • Biomimetics*
  • Catalysis
  • Light
  • Oxidation-Reduction

Substances

  • Alkaloids