Regioselective preparation of 2-substituted 3,4-diaryl pyrroles: a concise total synthesis of ningalin B

J Org Chem. 2002 Dec 27;67(26):9439-42. doi: 10.1021/jo026445i.

Abstract

Methylisocyanoacetate undergoes a 2 + 3 cycloaddition with alpha,beta-unsaturated nitriles to provide a regioselective synthesis of 2-substituted 3,4-diaryl pyrroles. The ease of preparation of alpha,beta-unsaturated nitriles allows the rapid synthesis of pyrroles with varied substituents. Using this method, a key intermediate (1) for the synthesis of the marine natural products lukianol A, lamellarin O, and lamellarin Q was prepared in two steps. A total synthesis of ningalin B (11) was also accomplished utilizing this methodology.

MeSH terms

  • Catalysis
  • Combinatorial Chemistry Techniques*
  • Heterocyclic Compounds, 3-Ring / analysis
  • Heterocyclic Compounds, 3-Ring / chemical synthesis*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pyrazoles / chemical synthesis
  • Pyrroles / analysis
  • Pyrroles / chemical synthesis*
  • Stereoisomerism

Substances

  • Heterocyclic Compounds, 3-Ring
  • Pyrazoles
  • Pyrroles
  • lukianol A
  • ningalin B