Palladium(II)-catalysed total synthesis of naturally occurring pyrano[3,2-a]carbazole and pyrano[2,3-b]carbazole alkaloids

Org Biomol Chem. 2014 Jun 21;12(23):3866-76. doi: 10.1039/c4ob00367e.

Abstract

Seven naturally occurring pyranocarbazole alkaloids (pyrayafoline A-E, O-methylmurrayamine A and O-methylmahanine) have been obtained by total synthesis using a palladium(II)-catalysed oxidative cyclisation of a diarylamine to an orthogonally diprotected 2,7-dihydroxycarbazole as key step.

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Carbazoles / chemical synthesis*
  • Carbazoles / chemistry
  • Catalysis
  • Chemistry, Organic / methods*
  • Molecular Conformation
  • Palladium / chemistry*
  • Pyrans / chemical synthesis*
  • Pyrans / chemistry

Substances

  • Alkaloids
  • Carbazoles
  • Pyrans
  • carbazole
  • Palladium