Synthesis of (+)-luzofuran and (-)-ancistrofuran

J Org Chem. 2014 Feb 7;79(3):880-7. doi: 10.1021/jo402790x. Epub 2014 Jan 22.

Abstract

The first synthesis of the furan-containing snyderane, (+)-luzofuran, is reported. The key step in this approach was an electrophilic brominative cyclization, which was accomplished using a nucleophilic N-heterocycle-flanked phosphoramidite catalyst in combination with the common laboratory reagent N-bromosuccinimide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bromosuccinimide / chemistry*
  • Catalysis
  • Cyclization
  • Furans / chemical synthesis*
  • Furans / chemistry*
  • Indicators and Reagents / chemistry
  • Molecular Structure
  • Organophosphorus Compounds / chemistry*
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Stereoisomerism

Substances

  • Furans
  • Indicators and Reagents
  • Organophosphorus Compounds
  • Sesquiterpenes
  • ancistrofuran
  • luzofuran
  • phosphoramidite
  • snyderane
  • Bromosuccinimide

Grants and funding

National Institutes of Health, United States