Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate

J Am Chem Soc. 2011 Oct 12;133(40):15797-9. doi: 10.1021/ja206538k. Epub 2011 Aug 11.

Abstract

We report the first total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate. Our route features a number of key transformations, including an indolyne cyclization to assemble the [4.3.1]-bicyclic scaffold, as well as a late-stage intramolecular nitrene insertion to functionalize the C11 bridgehead carbon en route to the natural product.

Publication types

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

MeSH terms

  • Chemistry Techniques, Synthetic
  • Cyanobacteria / chemistry*
  • Cyclization
  • Indole Alkaloids / chemical synthesis*
  • Indoles / chemical synthesis
  • Indoles / chemistry
  • Stereoisomerism

Substances

  • Indole Alkaloids
  • Indoles
  • N-methylwelwitindolinone C isothiocyanate