Iminonitroso Diels-Alder reactions for efficient derivatization and functionalization of complex diene-containing natural products

Org Lett. 2007 Jul 19;9(15):2923-6. doi: 10.1021/ol071322b. Epub 2007 Jun 30.

Abstract

A remarkably efficient method for derivatization of complex diene-containing natural products by using stabilized iminonitroso Diels-Alder reactions is described. Turimycin H3, ergosterol, reductiomycin, isoforocidin, colchicine and thebaine were found to react with nitrosopyridines in a highly efficient regio- and stereoselective fashion. Preliminary bioactivity evaluations of turimycin cycloadducts are reported.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemistry*
  • Crystallography, X-Ray
  • Imines / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Nitroso Compounds / chemistry*

Substances

  • Biological Products
  • Imines
  • Nitroso Compounds