Enantiospecific total synthesis of N-methylwelwitindolinone D isonitrile

Angew Chem Int Ed Engl. 2013 Nov 18;52(47):12422-5. doi: 10.1002/anie.201307464. Epub 2013 Oct 2.

Abstract

The total synthesis of N-methylwelwitindolinone D isonitrile (1) has been achieved in 17 steps from a readily available carvone derivative. The route features a double C-H functionalization event involving a keto oxindole substrate to introduce the tetrahydrofuran ring of the natural product.

Keywords: C-H functionalization; natural products; nitrene insertion; total synthesis; welwitindolinone.

Publication types

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

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Carbon / chemistry
  • Crystallography, X-Ray
  • Cyclization
  • Cyclobutanes / chemistry
  • Hydrogen / chemistry
  • Imines / chemistry
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry
  • Molecular Conformation
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry
  • Stereoisomerism

Substances

  • Biological Products
  • Cyclobutanes
  • Imines
  • Indole Alkaloids
  • N-methylwelwitindolinone D isonitrile
  • Nitriles
  • phenylnitrene
  • Carbon
  • Hydrogen