Total syntheses of menisporphine and daurioxoisoporphine C enabled by photoredox-catalyzed direct C-H arylation of isoquinoline with aryldiazonium salt

J Org Chem. 2014 Nov 7;79(21):10682-8. doi: 10.1021/jo5020432. Epub 2014 Oct 24.

Abstract

Isoquinoline alkaloids are attractive natural products due to their diverse chemical structures as well as remarkable bioactivities. Herein, we report the concise total syntheses of two isoquinoline alkaloids, menisporphine and daurioxoisoporphine C, through a mild and efficient photoredox-catalyzed direct C-H arylation of isoquinoline core with aryldiazonium salt. This new strategy is complementary to the conventional isoquinoline synthesis and would provide us a useful means to achieve a more convergent and flexible approach to access diverse isoquinoline structures.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products
  • Catalysis
  • Hydrogen Bonding
  • Isoquinolines / chemical synthesis*
  • Isoquinolines / chemistry*
  • Molecular Structure
  • Onium Compounds / chemistry*
  • Oxidation-Reduction
  • Photochemical Processes
  • Salts / chemistry*

Substances

  • Biological Products
  • Isoquinolines
  • Onium Compounds
  • Salts
  • daurioxoisoporphine C
  • isoquinoline