Total synthesis of oxidized welwitindolinones and (-)-N-methylwelwitindolinone C isonitrile

J Am Chem Soc. 2012 Jan 25;134(3):1396-9. doi: 10.1021/ja210837b. Epub 2012 Jan 11.

Abstract

We report the total synthesis of (-)-N-methylwelwitindolinone C isonitrile, in addition to the total syntheses of the 3-hydroxylated welwitindolinones. Our routes to these elusive natural products feature the strategic use of a deuterium kinetic isotope effect to improve the efficiency of a late-stage nitrene insertion reaction. We also provide a computational prediction for the stereochemical configuration at C3 of the hydroxylated welwitindolinones, which was confirmed by experimental studies.

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

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Cyanobacteria / chemistry
  • Hydroxylation
  • Models, Molecular
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Alkaloids
  • Biological Products
  • N-methylwelwitindolinone C nitrile