Synthesis of tetrahydropyrroloiminoquinone alkaloids based on electrochemically generated hypervalent iodine oxidative cyclization

Org Lett. 2010 Feb 5;12(3):436-9. doi: 10.1021/ol902566p.

Abstract

An approach to the synthesis of the tetrahydropyrroloiminoquinone alkaloids has been developed and applied to the preparation of N-1-beta-D-ribofuranosyltetrahydropyrroloiminoquinones. The strategy utilizes oxidative cyclization of aryl-methoxyamides by hypervalent iodine to construct the quinoline framework shared by members of this alkaloid family. The hypervalent iodine oxidant is generated in situ by anodic oxidation of iodobenzene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry*
  • Alkaloids / pharmacology
  • Animals
  • Catalysis
  • Drug Resistance, Neoplasm / drug effects
  • Drug Screening Assays, Antitumor
  • Female
  • Humans
  • Iodobenzenes / chemistry
  • KB Cells
  • Marine Biology
  • Mice
  • Molecular Structure
  • Monosaccharides / chemical synthesis*
  • Monosaccharides / chemistry
  • Monosaccharides / pharmacology
  • Oxidation-Reduction
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Pyrroles / pharmacology
  • Pyrroloiminoquinones / chemical synthesis*
  • Pyrroloiminoquinones / chemistry
  • Pyrroloiminoquinones / pharmacology
  • Stereoisomerism
  • Topoisomerase II Inhibitors

Substances

  • Alkaloids
  • Iodobenzenes
  • Monosaccharides
  • N-1-beta-D-ribofuranosyldamirone C
  • N-1-beta-D-ribofuranosylmakaluvamine I
  • Pyrroles
  • Pyrroloiminoquinones
  • Topoisomerase II Inhibitors
  • iodobenzene