Total syntheses of murrayamine E, I, and K

J Org Chem. 2015 Jun 5;80(11):5666-73. doi: 10.1021/acs.joc.5b00630. Epub 2015 May 12.

Abstract

We describe efficient synthetic routes to murrayamine A (mukoenine C), O-methylmurrayamine A, mahanine, O-methylmahanine, and murrayamine D and the first total syntheses of murrayamine E, I, and K. Key steps are a palladium-catalyzed construction of the carbazole framework and an annulation of the pyran ring, which is either catalyzed by phenylboronic acid or promoted by a Lewis acid.

MeSH terms

  • Alkaloids / chemistry*
  • Carbazoles / chemical synthesis*
  • Carbazoles / chemistry*
  • Catalysis
  • Lewis Acids / chemistry*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alkaloids
  • Carbazoles
  • Lewis Acids
  • O-methylmurrayamine A
  • mahanine
  • carbazole