Regioselective intramolecular reactions of 2-indolylacyl radicals with pyridines: a direct synthetic entry to ellipticine quinones

J Org Chem. 2005 Oct 28;70(22):9077-80. doi: 10.1021/jo0514974.

Abstract

[reaction: see text] 2-Indolylacyl radicals generated from the corresponding selenoesters under hexabutylditin-hnu conditions undergo regioselective intramolecular reaction with unprotonated pyridines to give polycyclic indolylpyridyl ketones. For substrates bearing a (3-pyridyl)methyl moiety connected to the 3-position of the indole ring, the cyclization provides easy access to ellipticine quinones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Ellipticines / chemistry*
  • Esters / chemistry
  • Free Radicals
  • Indoles / chemistry*
  • Molecular Structure
  • Pyridines / chemistry*
  • Quinones / chemical synthesis
  • Quinones / chemistry*
  • Selenium / chemistry

Substances

  • Ellipticines
  • Esters
  • Free Radicals
  • Indoles
  • Pyridines
  • Quinones
  • ellipticine
  • Selenium