A concise total synthesis of the natural carbazole clauraila A

Nat Prod Res. 2013;27(19):1749-56. doi: 10.1080/14786419.2012.751599. Epub 2013 Mar 12.

Abstract

A short and efficient total synthesis of naturally occurring carbazole clauraila A (1) is described. The approach is designed on the basis of the key regioselective Diels-Alder reaction of the properly substituted exo-2-oxazolidinone diene 3 with acrolein (4) to give the corresponding adduct 2. The latter is converted to functionalised diarylamine 8, which is cyclised to the desired carbazole 1 through a Pd-promoted or -catalysed double C-H bond activation process in a fairly good overall yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis
  • Alkaloids / chemistry
  • Carbazoles / chemical synthesis*
  • Carbazoles / chemistry
  • Catalysis
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Stereoisomerism

Substances

  • Alkaloids
  • Carbazoles
  • clauraila A
  • carbazole