Progress toward a biomimetic synthesis of phomoidride B

Org Lett. 2002 May 2;4(9):1451-4. doi: 10.1021/ol025595c.

Abstract

[reaction: see text]. An intramolecular cyclization strategy for effecting a biomimetic synthesis of the core structure of the fungal secondary metabolites phomoidrides A and B is described. The cyclization substrate 20 is prepared in eight steps from dibromide 10. Treatment of 20 with triethylamine in acetonitrile results in a rapid cyclization to give 21 and 22 in good yield.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Catalysis
  • Cyclization
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Maleic Anhydrides / chemical synthesis*
  • Maleic Anhydrides / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Penicillium / metabolism

Substances

  • CP 263114
  • Indicators and Reagents
  • Maleic Anhydrides